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The prospects of information technology for a feasible, functioning anarcho-syndicalist democracy

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The prospects of information technology for a feasible, functioning anarcho-syndicalist democracy
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Holmes, Curtis D
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vii, 75 leaves : ; 29 cm

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Anarchism ( lcsh )
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Technology and state ( fast )
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bibliography ( marcgt )
theses ( marcgt )
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Includes bibliographical references.
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Submitted in partial fulfillment of the requirements for the degree, Master of Arts, Department of Political Science.
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by Curtis D. Holmes.

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|University of Colorado Denver
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Full Text
THE PROSPECTS OF INFORMATION TECHNOLOGY FOR A
I
FEASIBLE, FUNCTIONING ANARCHO-SYNDICALIST DEMOCRACY
by
Curtis D. Holmes
I
B.A., University of Denver, 1984
A thesis submitted to the
Faculty of the Graduate School of the
University of Colorado in partial fulfillment
of the requirements for the degree of
Master of Arts
Department of Political Science
1991


This thesis for the Master of Arts
degree by
Curtis D. Holmes
has been approved for the
Department of
Political Science
by

Date


Holmes, Curtis D. (M.A., Political Science)
The Prospects of Information Technology for a Feasible, Functioning Anarcho-
Syndicalist Democracy
Thesis directed by Professor Michael S. Cummings
Many anthropological and political researchers have demonstrated that societies
approximating the anarcho-syndicalist ideal of functional authority without coersion by
the state, and of functional economic subgroups where members share radical equality,
exist in small-scalle, low-technological groups. The central focus of this thesis is the
prospect of complex information technologies providing a means to organize a feasible,
functioning society approximating the same anarcho-syndicalist ideal in mass,
developed groups. Caution must be exercised when speculating along these lines by
applying social science methods to meet some minimum standard of logical coherence
and consistency, and by identifying key concepts and lines of inquiry that are central to
the constructs of such a society. Visions of the good political society have
traditionally taken the form of utopian fictional literature. I use the precedent of that
tradition to construct a vision of that society, followed by an analysis of the vision as
I
related to its utopian theoretical, technological, and anarcho-syndicalist characteristics
and requirements. Throughout each element of analysis, utopian, technological, and
i
anarcho-syndicalist, I demonstrate criteria that the political vision meets, and limits that
it functions within. While too broad to consist of a proof that such a society is feasible
and functional, I conclude that the prospects indicated by analysis within these core
areas are favorable. There is no implied moral imperative that such a society should
arise, only that it is possible and desirable under certain conditions and circumstances.
The form and conten^frhiyhstrac^ryDBmved^recommend its publication.
Signed,
LChael Cummings


I
Dedicated to the memory of Vincent and Olive Holmes.
I
I


CONTENTS
Acknowledgements...................................vi
CHAPTER
1. INTRODUCTION..................................1
2. THE PROSPECTS VISION........................9
3. THE UTOPIAN ANALYSIS.........................27
4. THE TECHNOLOGICAL ANALYSIS...................40
5. THE ANARCHO-SYNDICALIST FOUNDATION...........58
6. CONCLUSION...................................70
BIBLIOGRAPHY.......................................72
INDEX......!.......................................75
v


ACKNOWLEDGEMENTS
I would like to thank the Political Science Department of the University of Colorado
at Denver and Dr. Michael S. Cummings, Dr. Joel C. Edelstein, Dr. Glenn Morris, and
Dr. Thad Tecza in particular for a challenging and inspirational learning experience and
dialogue, and also for the opportunity to pursue speculative theory. I wish to thank
Kevin W. Perizzolo, Leslie Petrovski, Mary V.G. Lindesmith, and Roxanne Birlauf
for their much needed assistance and patience. I give special thanks to Ron Strube,
Esq., for more personal inspiration and insightfulness than can be expressed. Finally, I
wish to thank all the friends, family, and colleagues who have encouraged and
supported the dissident and somewhat cranky views of a professional malcontent


Nihil motum ex antiquo probabile est: Distrust all innovations, wrote
Titus Livius. Undoubtedly it would be better were man not compelled to
change, but what! Because he is bom ignorant, because he exists only on
condition of gradual self-instruction, must he abjure the light, abdicate his
reason, and abandon himself to fortune? Perfect health is better than
convalescence. Should the sick man therefore, refuse to be cured? Reform,
reform!:cried ages since, John the Baptist and Jesus Christ. Reform, reform!
cried our,father fifty years ago. And for a long time to come we shall shout,
Reform, reform!
Pierre Joseph Proudhon, Property and Revolution
Vll


CHAPTER 1
INTRODUCTION
Man the Utopia Maker
The name of the planet, presuming it has already received one, is
immaterial. At its most favorable opposition, it may very well be separated from
the earth by only as many miles as there are years between last Friday and the
rise of the Himalayasa million times the readers average age. In the
telescopic field of ones fancy, through the prism of ones tears, any
particularities it presents should be no more striking than those of existing
planets. A rosy globe, marbled with dusky blotches, it is one of the countless
objects diligently revolving in the infinite and gratuitous awfulness of fluid
space. (Nabokov, 1958, p. 160)
When I first read this initial paragraph of a short story by Vladimir Nabokov, it
struck me like the lost chordthe most perfectly rendered paragraph of English
language that I had read. It has continuously transformed its meaning for me, and it
strikes me now as a perfect description of the way that people project the world as it
should be through their imagination. It is both universally general, a world that
approximates our own enough to be clearly recognizable, and detailed, radically
differing to contrast the daily is with the ought
Jacob Bronowski in his essay exploring the nature of cultural evolution, The Ascent
of Man, discusses the unique psychological trait of humans of foresight.
So far, there is nothing to distinguish the athlete from the gazelleall that
in one way or another, is the normal metabolism of an animal in flight But
there is a cardinal difference: the runner was not in flight The shot that set him
off was the starters pistol, and what he was experiencing, deliberately, was not
fear but exaltation... .In themselves, his actions make no practical sense at all;
they are an exercise that is not directed to the present The athletes mind is
fixed ahead of him, building up his skill; and he vaults in imagination into the
future. (1973, p. 36)


From this ability to envision the future, people have contemplated and projected a
meliorated political and economic society for all recorded history. In the Western
scholarly tradition, Thomas More gave us the long-standing name, Utopia. But in
Utopia, as later on, we find the Thomas More who saw the world as a wicked place
and the human heart as a pit of darkness requiring the light of diligent public scrutiny if
the monsters lurking there were not to crawl out and devour the person and the society.
More began Utopia in a church (Marius, 1985, pp. 154-155). Mores genesis of
Utopia in a church is prophetic of a long history in Western utopian thought of anti-
establishment establishmentarianism. The effort to reform the ills of the world often
results in outrage at the state of current institutions because they are not ones that we
envisionso the Utopians propose new institutions to replace them. I call attention to
this aspect of utopian literature, because I would like to distance the thesis from it. The
I
thesis does not assume the necessity of absorbing the individual into some collective
will or reformed communal institution to retain utopian characteristics. It does not, as
More does, criticize immoral or inefficient social institutions by deifying others, but
rather measures the power of utopian vision by comparing means and ends and their
relationship to one another.
The notion of the meliorative perfectibility of people and their society always begs
the question of present circumstanceshow did we get here and where to go from
here. The Utopian1 nature of this thesis dwells on the political will of individuals in
society to shape ends and means, not on the perfectibility of either.
The Role of Information Technology
Politics is dependent on communication, and communication is limited by a number
of factors and characteristics of reality as we know it. Geography and the limits of
2


I
people to travel are two of the most important; diversity of language and culture are
others. The purpose here is not to identify and itemize a list of limiting factors, but
rather to recognize that homo faber, man the maker, by the ability to conceive a technos
has continuously remade the nature and scope of those limiting factors. The products of
the hand of people, technology, are intimately linked with communicadon and politics
and in many cases provide the imaginative qualities and the limiting reality of utopian
political visions.
The relationship of technology to politics is often only explored on the surfacethe
way that innovation, assessment, control, production and so on are influenced by the
political environment and how political organization (e.g., bureaucracy) can affect
technological development. Yet the relationship extends far deeper and wider. It exists
at the level of political form and control itself. And, in turn, political form determines
not simply the efficiency of production of this years Christmas gift fad, but the
existence and nature of how progress is defined and the costs that society is willing to
pay for the production of goods.
In The Control Revolution, James Beniger describes in more detail the specific type
of technology that I am interested in, information technology, and its relationship to
social control.
Because both the activities of information processing and communication
are inseparable components of the control function, a societys ability to
maintain controlat all levels from interpersonal to international relationswill
be directly proportional to the development of its information technologies,
(cited in Teich, 1990, p. 54)
One of the ongoing and sharply divided battles in the discussion of issues
concerning technology is its inherent nature: good, bad, neutral, all of these?
Therefore, in this discussion of computer and information technologies and how they
3


interact with political structures, the perspective called techno-structuralist, elaborated
by Tehranian will be used. (1990, pp. 212-217) In this viewpoint, technologies are
neither good, bad, nor neutral in and of themselves. This is because they developed
out of institutional needs (in the case of information technologies, primarily military and
business needs) and their impact is always mediated through the institutional
arrangements and social forces... (Tehranian, p. 5). In other words, technologies
always feed into the social and institutional paradigm and have good, bad, and neutral
effects. It is the way that the paradigm uses and understands the technologies that will
i
determine the greatest effect of that technology.
Computers, especially when linked to other information technologies, have both
centralizingcontrol, privileged, barrier ridden and decentralizinguniversal,
autonomous, and democratic characteristics. Those characteristics develop in
accordance with the nature of the environment of computer use and the time and place
of use. The promise of computer information technology is the revitalization of a form
of direct democracy and autonomous decision-making; the peril, a highly centralized,
controlled totalitarian state (with a level of totalitarianism perhaps yet unseen).
Prospects also exist for transformation of politics into new forms of association that
are less possible or limited by the scale of societies in the absence of computerized
information technologies. Tehranian discusses this aspect of computer politics in terms
of a Communitarian Democracy. As extensions of our senses and as leverages of
power, technologies replicate as well as augment the existing power relations.
(Tehranian, 1990, pp. 201-212) In its ability to augment, Tehranian discusses the
Green movement in West Germany and the Sarvodaya movement in Sri Lanka as case
studies of communitarian value movements or parties whose potential for large-scale
4


reproduction and political power has grown and developed along with the information
technologies.
i
i
An important political analysis that must be included in any exploration of current
and future political implications of the computer, at the national level in particular, is
social choice theory, presenting mathematical and logical limits to computational
aggregation and computer politics.
Technology can indeed make democracy possible in places where it was not
possible before. But the possibilities are not boundless. The bounds are set not by
technology but by logic (McLean, 1989, p. 2). Assessment of computer politics is
based then on the limits to the very logic systems of which computers are built, but we
must assume that new logic systems can and will be created that we cannot yet account
for nor anticipate.
The Anarcho-Syndicalist Model
The thesis final conceptual element is the foundation of the political theory vision
of the social and economic system that I argue can be created given the political will to
integrate information technologies into political decision-making and to dismantle
current institutions. I have chosen as an historical basis the views of anarcho-
syndicalists with democratic variations. Anarchism speaks to the political questions of
property, the state, and the relations between the individual and the state. There was
perhaps never an anarchism, but many anarchisms, and they have contributed more in
the areas of social critique and political philosophy than in any practical and long-lived
organizations and associations. Yet practical political application of a philosophy is only
one part of its value and not necessary for some form of validity. But for this thesis it is
5


a critical requirement that practical application and continued functioning be possible
I
that is where I will flesh out the path I think possible.
The syndicalist side speaks to the economic questions of ownership, material
I
wealth, need, supply, production, consumption and the link between the economic
i
environment and the structure of living. Trade unionism was the focus of syndicalist
thought historically, but I have taken the philosophy to what I consider its logical
conclusions in worker-owned and democratically managed firms. Information
technology is not only an integral part of the operation of such firms but also implies a
certain level of production, technological development, and growth that must be
explored to have a full picture that answers questions concerning sustainability. There
are also two important questions about the parameters of democratically managed firms:
(1) What are appropriate decisions that society as a whole needs to makethe
macroeconomic questions, and (2) What are appropriate decisions that organizations at
the level of the firm need to makethe microeconomic questions.
William Goodwin in Rights of Man and the Principles of Society practically ignores
the question of economics and favors a rational analysis based on individual
psychology. This is how he builds his vision of anarchy and radical egalitarianism. He
states, Society is nothing more than an aggregation of individuals (Horowitz, 1964,
p. 113). Yet it is'that aggregatefor which we invented a word, society, that also must
be accounted for1 and its characteristics included in any feasible theory of anarchism.
Pierre Joseph Proudhon analyzes from the perspective of Justice (later also reflected
I
in the work of Rawls) and states in Property and Revolution,
These then are the three fundamental principles of modem society,
established one after the other by the movements of 1789 and 1830:
1) Sovereignty of the human will; in short, despotism. 2) Inequality of wealth
and rank. 3) Propertyabove JUSTICE, always invoked as the guardian angel
6


of sovereigns, nobles, and proprietors; JUSTICE, the general, primitive,
categorical law of all society. (Horowitz, 1964, p. 106)
In anarchism and syndicalism the question is always authority, but the analysis
i
revolves around the nature of the individual and the nature of the aggregate we call
society. And, along with Proudhon, that analysis must study sovereignty, equality
(political and economic), and property.
These then are the three braids, utopian political analysis and theory, information
technology, and anarcho-syndicalist structure, that will be weaved together here to
create a vision, and an analysis of that vision, for a new society. I intend to demonstrate
that such a society is feasible and functional and that information technologies make it
possible to sustain that vision in a mass, developed, and industrialized society. While
all three braids ajre vast areas, I have attempted to focus on the most important aspects
and criteria of each that applies to the main thesis.
From Ovid (1st century BC to 1st century AD) through Plato, More, Bellamy, and
Orwell, and from utopia to dystopia, political writers have found that a literary
expression of their visions proves more effective and appropriate than political
exposition or methodological social science. The literary style or form has a power to
conjure a world whole and communicate that world more directly than might be the case
with methodological exposition. This does not imply that there is a lack of method or
valid analysis in ^utopian expression, only that the style of choice differs substantially
from scientific papers. Following that tradition, I present a fictional account of the
political and economic information society I see as an option. The method will follow.
!
The fiction and the analysis explicitly treat the individual as primarily a rational actor
and the view of that individual of the prospects for alternative systems as minimalist. If
the implementation of information technology along the lines explored would in and of
itself at a minimum level lead to greater freedom for the individual even without
7


transforming the society and systems, then it is assumed a sufficient rationale for
following that model. While developmental transformation possibilities exist with
information technology and are explored peripherally, those possibilities are not
primarily important in the discussion of this thesis.
8


CHAPTER 2
THE PROSPECTS VISION: A FICTIONAL JOURNEY
The earth turning with its perpetually awakening inhabitants creates dawn as it has
been doing and still continues to do; but the people, those groggy, flea-bitten, poor,
rotten, conscious thinkers, ah, they had to discover that the sun never rises, that the sun
does nothing but what the sun does and is no Apollo, but rather a big ball of gas. And
Philemon, who prefers Phil, at present a lawyer on this little blue world, has a great
deal to do.
The trial committee had been formed several months ago by community decree and
Phil, contrary to: usual practice, had volunteered to be case presenter. His skills were at
least rusty after his years of teaching at the local learning center, yet he couldn't help
but be intrigued by the monster in their midst as the press so jubilantly termed her.
The questions brought to mind by this case were legion. They propagated,
overpopulated the legal mind and spilled, barren, into the quiet township street
Daybreak is always the most productive thinking time for him, but today proved to
be that irritating exception. He flicked the touchplate on the wall and waited for the
room to luminesce.
My Mother, Phil thought, always warned me about thinking and dressing at the
same time. Focus, she always insisted, focus on what you need from the world or it
will ignore you my little. He pulled on his typical jumpsuit, a thin grey coverall that
had become the standard dress of the day. Dressing actually proved to be a simple affair
since people had let fashion and its constant change and frivolity pass into history. The
one remnant of individuality was the personal vest that most people weaved, dyed or


painted themselves, or with mother's help, and wore over the jumpsuit He pulled it
on, his thinking [distracted by the pattern.
A full crest on the right side of the vest overpowered the remainder of the cloth. He
had found this crest, a black and red circle with birds, long ago in a book he had been
i
reading for entertainment. The pattern vibrated before his eyes and captured his
imagination then as it now captured his attention. He had decided then and there to add
it to his vest as the powerful symbol of his future life. He didn't need to understand it;
its meaning was forgotten anyway; it was the power he sensed in it that he wished to
possess for his life.
He flicked the touchplate and left. First on the day's agenda was a visit to the
learning center to arrange an indefinite absence. It was fairly routine, especially for case
presentation, but, he suspected, the case and his role would become the talk of the
community, which constantly led him to question his own motives in this affair. It had
been, after all, several years since he last presented, and many would have wanted to
argue this case. His almost ridiculous mythological stature in the community guaranteed
his admission; however, when he chose to volunteer, he also made many mighty
enemies at a stroke.
Rounding the adobe-like passageway to the center he stopped shortly to adjust his
attitude to focus on the volley to come. Diana Strand, or S as she was known, would
be the difficult and hurt victim in the drama around the comer. She was the center of a
four-way marriage in the village and had been manipulating for what seemed decades to
make Phil the fifth. She was sure to see his mad rush to volunteer for this case as a
i
desperate escape attempt from her, such was the narrowness of her thoughts. Quickly
he tried to concoct some simple formula to try to open her awareness enough so that
she might see that this case was much more to him than everyday life and a simple
10


appetite for adventure. But formulas wouldn't do. Her life was her marriage and the
quadrangle politics that emerged from it His concerns, thoughts, worries were beyond
her scope; he had to leave her with that at least.
S, I need to talk with youperhaps in private would be best.
She remained quite calm yet verbally pounced his intrusion.
Can't you see, I'm teaching class?
S lowered her eyes and walked, shuffling, to the doorway.
I'm sorry; I didn't intend to be so terse, Phil. It's just that we needn't discuss it.
I'll talk to you after the trial.
The battle not fought, he reflected, can't be lost.
***
Phil stepped, into an individual commuter car to drive to an interview and do some
research about 60 miles from the village. The car operated on solar energy and had been
built to last12 years so far for this one. When he was younger and had little income
credit to use, Phil had entered into an agreement at one of the production factories that
manufactured the cars. He worked in the factory for about four months producing the
vehicles in order to drive off with one. Even though the cars were not privately owned,
they still represented quite a labor and material commitment in the community and
required relatively high amounts of credits to operate. The benefit, however, of
considering the complete transportation system as a public goodincluding vehicles
had worked to the communitys advantage. Rather than a consumable good, vehicles
were now planned and produced as a capital good and engineered for extended lifetimes
to provide the most transportation and communication for the economic input.
The factory experience had been the first time that he had become a member of a
firm, even though this was by special temporary arrangement. The engineers at this
11


firm had devised the first operational production system for solar-powered vehicles that
needed extraordinarily little battery storage. What storage capacity there was, usually
was only needed for short periods of time in the worst of weather. Even most overcast
days provided enough convertible energy to power the vehicle.
His arrival at the plant was made official by a two-thirds vote of acceptance by all
the worker-owners of the plant. Even though this kind of temporary work agreement
had become fairly common practice, this factory continued to exercise full voting
requirements for ratification of every new worker-owner. The vote was taken within
the first fifteen minutes of the day when all the policy and day-to-day administrative
business was performed at computerized information workstations available throughout
the plant This real-time, on-line system allowed all 1,200 employees to communicate,
argue, and debate during the time limitations, and then to vote. The vote was tallied
almost instantaneously and the next agenda issue, agreed on the day before, became the
issue at hand. At the end of all the voting, a summary of all decisions and
administrative functions was provided to each person.
Although some factories had randomized worker-owner roles within the plant,
called facetiously by some, role de jour, this factory had decided on more traditional
elections for positions based on merit and testing. Those qualified could run for the
various administrative positions of trust and authority. The number of terms, however,
were strictly limited to one, and all office holders returned to other positions. The only
exception was the engineering department where the head engineer could only be
removed by a vote of no confidence. Such was the power of specialized knowledge.
The head engineer in this plant, however, received far lower income credits because of
his powerful position.
12


Phil had been extremely happy that this plant was not based on randomized roles as
he wouldnt have to be distracted by potentially being a candidate during every vote. As
a temporary employee, he preferred to work on the car to earn factory credits, rather
than in some administrative or specialized position.
He did fill in for a sick worker-owner for several days in the materials ordering
department just before leaving. He left with a mountainous headache daily as his
distaste for mathematics fought with his understanding. The ordering computer was
interlinked to many of the main materials suppliers of the factory and also to the central
ordering computer that any producer could link with. The computer kept constant track
of inventory and daily use, attempting to minimize warehousing. Phils job those few
days was to fmd needed materials on the computer market, order, and arrange for
transportation.
All the income credits and costs in terms of time and value were calculated based on
the agricultural supply. Phil mused while ordering a quantity of metal from a factory
up-river about his inability to understand how people had seriously placed value, real
value, in gold and other metals as carriers of economic worth. That could only happen
in an economy abundant with agricultural goods or in such authoritative control that
those without food had no avenue of action available.
The agricultural supply had been good this year, and the calorie allowance had been
going up for several yearssome claimed to ridiculous heights. At the time, calories
had become quite the controversy. Agricultural goods and value-added foods were also
available to all on the computer market, but you could only order a maximum calorie
equivalent of food. That limit had now become so high, that many people ordered the
most incredible amounts of chocolate cake and fat-added foods that many were calling
for factories to limit production of such goods.
13


The engineers at this and other vehicle production factories had taken the idea of the
i
vehicle as a capital social good so seriously and designed these solar commuters so well
that orders for the cars had considerably slowed within the last few yearsthus the
new temporary agreements arranged to moderate the necessity of decreasing work
before people chose to leave. It was, however, work that was reduced and not the
worker-owners numbers as the bull or the bear within the plant was borne equally by
all.
The plant had no legal status, such as a corporation, but rather operated under the
current rules and policies decided by the community as a whole. Often this made some
operations of the plant more difficult, but preempted the long-term abuse of loopholes
in legal semantics by a corrupt few. In fact, many of the factories and work
cooperatives changed status and structure often, sometimes evolving into groups that
bore little resemblance to their original function or purpose. Long-term stability and
purpose provided both a poor means for responding to change and a good environment
for developing institutionalized and abusive authority over others. The difficulties
inherent in constant change were understood to be a large part of the payment toward a
freer life.
His first dayiof work, Phil participated as a full worker-owner in setting the agenda
and making the decisions of the plants operations. His workstation began with the
agenda from the previous dayan election for a position that had opened after a
retirement, a vote on the reduction of the work day to 5.5 hours caused by dropping
demand, a rise in automobile pricing to compensate for lost income from the long-term
drop in demand, an arbitration vote on the complaints of the factory manager with the
current chief of material acquisition, and a setting of the next days agenda.
14


As a student of law at the local learning center, he was very interested in the
arbitration vote and how the factory handled such disputes. Apparently, all complaints
i
had to be made publicly before any remediation is possible. The factory manager had
accused the chief of under-ordering certain materials in the solar electronics department
to make the departments production figures look bad. Apparently, this was a personal
vendetta.
The charge had been made public at the plant several weeks before and a simple
majority of worker-owners had voted the charges severe enough to warrant
investigation and arbitration. A committee of three randomly chosen worker-owners
was established to conduct interviews and to review any appropriate documents. They
were given three weeks to report.
Both reports had been available on the main computer now for one week, and the
arbitration committee's report and recommendation was to be voted on. Phil took this
act very seriously and reviewed the committees recommendation, the statements of
both parties, and a dissenting view provided by an interested worker-owner. It seemed
to be fairly clear that the chief had been under-ordering certain materials that were
readily available on the computer market, but was less obvious as to why.
The under-ordering was enough of a concern to others in the plant that the vote
clearly favored the report of the committee that irregularities did exist The appropriate
response seemed to be removal of the chief, but other options were presented as well,
including community service and liquidation of his interest in the plant Moderation
won the day and he was simply removed from the role of chief of materials acquisition.
Another position at the plant was randomly chosen for him.
***
15


Phils wandering thoughts on that first arbitration case at the plant brought his mind
screaming back to the task before him. His research would take him to a small
agricultural and production cooperative about 60 miles outside of town. He was
approaching the cooperative and flipped on the map chart just to make sure he had the
correct one.
He checked the map display cursorily as it was obvious that the building on the
right, a large farmhouse surrounded by dormitory-style housing, was the cooperative
he was after. He pulled in and sat for a few minutes, building some strength and
rehearsing his questions.
Severn, the woman who was currently chief negotiator of the cooperative, appeared
at the main farmhouse door and waved him in. He had discussed his reasons for
coming several weeks ago on the phone but was unprepared for the brute strength and
presence she seemed to possess. They greeted traditionally, shaking hands.
Levy is in the main dining room waiting for you, she opened the conversation.
The cooperative discussed the problem at our last meeting and decided that he should
be relieved of duties until the case is completed. He has chosen to stay with us even
under these conditions. Be thorough, but dont drag this out
I appreciate your directness, Phil blurted in return, my intentions exactly.
Phil entered the dining room. Levy was very stoic, and volunteered no information,
i
the perfect reactive personality. When did you first meet her?
Levy seemed to slightly cross his eyes as he answered, I dont see that my life is
any of your concern.
I
You will be asked many questions at the trial, Phil added, you may as well get
some practice in now.
16


Levy evaluated his position and turned to the window answering every question
directly but without embellishment Yes, he had met and admired her. Yes, he knew of
her views, probaibly after the second meeting. Yes, they had met several times at night
at the cooperative. No, he was not a member of her group. No, he would not name
names. Enough practice.
I
Phil needed to access some public documents to substantiate members of the
cooperative and attempt to link others to her meetings in the dark. He asked to use the
farmhouse workstation and retrieved names of those he considered interviewing next
Severn had made it clear, however, that for now his presence had been tolerated long
enough. Work to do, she stated and opened that front door once again for Phil.
On his return trip Phil turned on the car radio and listened as each low-power
transmitter, some from cooperatives, some from small villages and towns, some just
individuals ranting, faded in and out on the main channels. Many were discussing the
upcoming trial, but luckily no one had used his name yet. Fame was rare in an age
where everyones 15 minutes of exposure to fame could stretch on indefinitely thanks
to full public media access. One cooperative, as it faded in, appeared to side with many
extremists, who, while not yet verbalizing it openly, were discussing the old uses of
the death penalty. If you couldnt pick up their not-so-subtle implication that it was time
to rethink the practice of forbidding death penalties, then you wouldnt realize the
serious implications of this case.
As the station faded out, the ashram Rama speeded into view and and retreated in
the mirror with the temple sign of an avatar-like character holding a handful of onions
and smiling somewhat awkwardly With over one million pounds of onions produced
last year, the avatar had a lot to smile about
17


Phil went directly home on his return to the city. He needed time to compile the
information he had been researching into something that resembled a presentable case.
The case was only three weeks away, and the jury had already been selected by
computer rote. He flicked the touchplate, and the small cottage began to luminesce from
the chemically stored energy from the days sunlight The cottage was a small, well
suited space for one person, and one of about fourteen cottages inhabited by those who
taught and worked at the learning center. The cottages were in a wooded area about a
mile from the learning center, far enough that Phil didnt feel as though he lived in his
classroom or at the center, yet close enough to walk or cycle.
Originally the learning center cooperative staff had worked and lived in a large
mansion-sized home they had built themselves, but they found the close proximity of
living and working led to frustration and anxiety. Some separation was required. It was
then that the community as a whole, including volunteer students, built the cottages as a
living settlement away from the center. It had proven much more effective, though
sometimes Phil thought even more distance would be an improvement
He scattered his research, interview tapes, press clippings, and assorted artifacts on
the floor.
***
Her name was Sharon, and it seemed she had always been somewhat precocious.
Her childhood, or what was known of it, didnt provide any stunning psychological
insights into her later activities, just a story of a very bright young woman with
ambition. Her learning-center activities were average, although the learning center she
had chosen to attend, while rigorous academically, had fought several accusations of
supporting violent student organizations that had disrupted local town meetings and
work communities. It had been asked to disband once, but refused, then reformed into
18


an exclusive organization that accepted no requests for admission. The admissions were
by invitation alone.
There were no indications that she had ever faced community sanctions, community
exile, or a called1 trial. Apparently while she was carrying on the gravest of her
activities, she had also contributed substantially to the communities of which she had
become a member and was one of the highest producers on the cooperative where Phil
had been conducting interviews. On the surface quite a model. But below that
surface...
***
The knock at the door brought Phil screaming back to consciousness. The room
spun and shattered into a thousand spinning fragments. The spinning slowed and began
to crystallize into a recognizable whole, fragment connecting to fragment until Phils
conscious mind looked out on a unified world that seemed to make some sense.
Knock. The door. He stumbled to the door and found S there, waiting impatiently.
Catching up on a little lost sleep? she grilled. Going to invite me in?
Phil only then realized that it was late evening, and he had fallen face-down asleep
into the piles of papers detailing the case. Oh, come on in, he said, and Ill put on
some tea.
He assumed that this was to be another assault on his timing for taking this case and
another blunt attempt to recruit him into her communal marriage, but his next thought
i
reminded him tKat she had given up cottage visits for this purpose long ago.
Ive come to tell you, she drawled, that I have been chosen by vote to be the
second case presenter and that we wont be able to have any contact after today.
What a relief, thought Phil. What an honor, he said. Isnt the community a little
behind schedule on appointments?
19


Yes, said S, but everyone feels that we must be careful on a case of this
magnitude. It shouldnt be rushed in any way. We wont be able to speak for quite
some time you know.
i
Uh-huh, said Phil, but it will be much easier since we wont be at the learning
center until the case is completedI think well manage.
After she left Phil looked at the cottage walls and the papers on the floor. Perhaps
the world doesnt make whole sense yet, he thought; need more sleep.
***
What makes this inquest significant is that these prisoners represent sinister
influences that will lurk in the world long after their bodies have returned to
dust They are living symbols of racial hatreds, of terrorism and violence, and
of the arrogance and cruelty of power. They are symbols of fierce nationalisms
and of militarism, of intrigue and war-making which have embroiled Europe
generation after generation, crushing its manhood, destroying its homes, and
impoverishing its life. They have identified themselves with ... (Jackson,
1947, p. 31)
i
Phil stood before the court committee, the reporter overseeing the accuracy of the
voice computers documentation of the case. Phil knew almost every workstation and
home would be requesting full transcripts of the case each day. He began by quoting
the paragraph from the first international war crimes trial in post-WWII Germany as a
precedent, even during the time of state domination of politics, addressing the problem
they were all about to confront in person.
He spoke alternatively to the jury, the defendant, and the judge in this case, Jane.
She was a member of an agricultural and small motor manufacturing community about
100 miles south of the city. She apparently had a reputation for having a strong intuitive
sense of justice and fairness and had been elected almost uncontested through three
I
court committees to act as judge in this trial. Her affect was stoic, and it was difficult to
detect even the slightest of expressions on her face. Phil had learned long ago when
20


practicing, however, that the limited role of the judge in modem cases didnt justify the
time expense of guessing the judge.
He began carefully presenting all the facts of the case as he had found them.
He explained the facts of her childhood, attendance at the academy and the
accusations against it, her family background, associations, aspirations. And then, he
delved into the crux of the case.
Apparently while working on the agricultural cooperative, Sharon had begun
forming discussion groups on political and business issues of the cooperatives. Were
they producing too much? Was the role of subsistence farming for vegetables at the
cooperative useful or a hindrance? But vegetable and aquaculture questions soon turned
to authority and culture questions and the group began to lose members because of her
tirades against radical equality, but gained others who had heard of her fiery speeches.
Phils interviews at the cooperative had demonstrated consistent stories of her flushed
face and rising voice tearing at the fabric of social life at the community and causing
serious dissentiqns among newly formed groups there. Soon an elite group of her most
ardent admirers formed, and when it was discovered they had been hoarding a
significant amount of their production, they were asked to leave the community.
But this was just the beginning. She wanted to form a core of radical loyalists that
she could train to carry out her final solution; she wanted to build an armed group of
shock troops who would begin to expropriate land and people for their new society.
Those that wouldnt follow, wouldnt live.
The arms stash that had been found buried at a small privately leased farm about 20
miles from the cooperative had been designed and built by her and the man everyone
considered second in their secret society. They had used expropriated equipment and
material from the manufacturing section of another local commune that produced small
21


farm implements and machinery. They had developed molds and had manufactured a
variety of short-fange and long-range weaponry to meet the needs of her developing
master plan to conquer and rule. They had also produced a great deal of ammunition
and explosive devices through several worker-owners at a materials factory 200 miles
south of the city: This, above all, stated Phil, demonstrates the extent of her
malevolent infiltration of our lives and our communities.
i
Witnesses then were called and facts substantiated. Faces turned in horror and awe
as the extent of the threat she had posed and the close proximity of her soon-to-be-
launched authoritarian war became clearerthe monster in our midst.
The judge pointed at Phil. Have you completed presentation?
Yes, he returned as she then pointed in the direction of S.
Second case presenter.
Phil listened as S presented a scenario vastly different from his own. This was
relatively unusual, especially in cases this well researched, as neither presenter acts as
advocate for anyone but rather for the truth and the case committee. Most cases would
show one presenter pointing out differences in fact that needed to be resolved or
presenting different or more information and interviews that tended to substantiate the
validity or invalidity of the charges against an individual or group. Phil couldn't help
but wonder if S wasnt taking this opportunity to humiliate him personally for his
marriage reluctance.
S portrayed an ambitious and acrid personality in Sharon, but one that did not
deviate at all from the norms of an egalitarian and open society. The small aims, while
of enormous concern, could not be directly linked to her except for testimony from
witnesses who themselves may be guilty of the offense and attempting to escape
justice. As for her advocacy of a more authoritarian system, belief in such a system had
22


long ago ceased to be classified as an offense, and she had been free to create such a
l
system within the structures of this society as long as participation was stricdy
voluntary, as Phils presentation had clearly demonstrated was the case.
i
S also continued, demonstrating that in fact there was no provable conspiracy, that
witnesses continued to profess that the monster had indeed continued to participate in
i
both the decision-making functions of the firms and cooperatives of which she had
been a member and the daily social policy-making functions. How could such a
supposed monster whose beliefs were the antithesis of the egalitarian ideal continue to
i
participate in such a system? And finally, there had been no acts or deeds committed by
Sharon or any of her followers that could be considered offenses. Phil thought about S
presentation and realized that even a callous belief that she was acting out of personal
revenge couldnt discard the points she had raised. He thought she had thrown quite the
monkey-wrench into the portrait the press had pieced together of this affair, but little
did he know the whole case was about to blow wide open.
After both presentations, the judge pointed to Sharon and asked if she would like to
present her views and facts of the case to the jury. Indeed, she did. She began by
practically admitting all the established facts of the case, but then, in the described
fashion, her faceibecame beet red and the tirade began.
I challenge die very validity of this court, this case, these presenters, and any
verdict of a straw-picked jury, she railed. By your own beliefs how can you enforce
1
such a judgement, a verdict. How can you justify the coercive intrusion into my life and
welfare, and how will you enforce it except by physical force? Because, opposed to the
second presenter, I did construct and bury those weapons; I did form groups who
plotted murder and property seizure, and I will continue to build and plot until my last
breath. This society is no society. For you will have to destroy your society to enslave
23


me and control my actions and words. You will have to coerce and imprison and thus
end your ideal, 6r I will destroy it for you in a true society of rule by those who merit it;
and it will have more wealth than your worker-owners, as jittery and gutless as birds
who scatter at every step, can ever imagine. You will end non-authoritarianism and the
lack of a state with me, or I will do it for you. We find your soft Utopias as white / As
new-cut bread, and dull as life in cells, / O scribes who dare forget how wild we are, /
How human breasts adore alarum bells. / you house us in a hive of prigs and saints /
Communal, frugal, clean and chaste by law. / Id rather brood in bloody Elsinore / Or
i
be Lears fool, straw-crowned amid the straw. / Promise us all our share in Agincourt /
Say that our clerks shall venture scorns and death, / That future ant-hills will not be too
good / For Henry Fifth, or Hotspur, or Macbeth. / Promise that through tomorrows
spirit-war / mans deathless soul will hack and hew its way, / Each flaunting Caesar
climbing to his fate / Scorning the utmost steps of yesterday. / Never a shallow jester
any more! / Let not Jack Falstaff spill the ale in vain. / Let Touchstone set the fashions
for the wise / And Ariel wreak his fancies through the rain. (cited in Walters, 1989,
p. vii) With that, a raised fist, and chaos in the court, the day ended.
Phil didnt believe that one person who was in that court today, or anyone who read
: |
the transcripts at their workstation wasnt mulling about their whole society tonight as
he was. He could barely believe the power that Sharon had wielded in that room and
the danger that she represented. This was as close to a coup, he supposed, as any
society with no state apparatus could come. She had admitted her guilt and challenged
the court to find her guilty and then control her without destroying its own ideals. Yet it
had to be possible.
i
The court gathered again three days later as the jury had reached a verdict In his
meditative state about society, Phil wondered at the continuation of the belief that those
24


charged with offenses were entitled to face their accusers and the jury in person. It
would have been just as easy, if not easier, for the verdict to be polled at workstations
and the sentence carried out by a rote committee with the judges instructions. But here
they were in person, with a hundred-thousand people watching computer screens.
The jury read the guilty verdict and the judge began the sentencing act with an
explanation. The defendant is found guilty of violating some of the most precious
norms of our society. Contrary to her apparent belief, this is not a non-authoritarian
society, but rather one in which authority is decentralized to individuals and to the
aggregates that they voluntarily create. Those are the only legitimate modes of
authority. But confusing this decentralization with a lack of authority to meet challenges
to the continued equality and freedom of individual choice that you represent is to
mistake weakness for strength. Contrary to your argument that we must destroy our
most cherished beliefs to physically control you, we protect them. For we have not
institutionalized bur power and authority as you have done, and have not claimed any
elite right to authority as you have done, but act individually and as a voluntary
community to defend ourselves against those who would institutionalize their power
and set us on the road to greater inequality and less participation. We make mistakes,
but do not then defend our mistakes as a necessary and inescapable part of an
institution, but constantly tend toward correction. You have demonstrated that for your
own power, and those who follow you, you are willing to kill, injure, destroy, steal,
and coerce. You are hereby, banished to the internal urban cooperative where you and
others who have been previously banished are free to create your own society as you
see fit However, all materials are limited, you cannot leave the cooperative for life, you
will be provided with raw agricultural goods and implements only. This is the limit to
our authority, an eternal vigilance against you and those who wish to enslave all but a
25


minority of us as has been done in the past We exercise valid authority to protect
ourselves to maintain our society, not to destroy it, by preventing you from destroying
it in the name of some selfish glory at the expense of others. Do no harm, is not just a
physicians pledge, but our own. And, do not allow harm is its corollary.
Phil returned to the cottage and flicked the touchplate as he entered the room. The
sun was slipping under the horizon, that big ball of gas that had recharged the chemical
walls that now luminesced. He sat at the workstation to order new coveralls and two
new pairs of shoes for his return to the learning center tomorrow. The request almost
instantly entered the computer market that presented consumer demand and matched it
to current and projected firm supply. A shoe factory 40 miles outside of the city
matched the order and entered it into the production planning schedule for the next day.
They also automatically ordered enough material from raw producers to meet
tomorrows production demand, which was then picked up by a transportation
cooperative and charged back to the material supplier. At almost the same moment, a
second order for shoes arrived on the demand market from the internal urban
cooperative. The same process quickly fell into place with a second transportation firm
picking up the order for 10 percent less charge than the previous transportation
cooperative.
The earth turning with its perpetually drowsy inhabitants creates sunset as it has
been doing and still continues to do; but the people, those groggy, flea-bitten, poor,
rotten, conscious thinkers, ah, they had to discover that the sun never sets, that the sun
does nothing but what the sun does and is no Apollo but rather a big ball of gas.
26


CHAPTER 3
THE UTOPIAN ANALYSIS
Is Utopia Serious?
Chapter 3 presents an exploration of utopia as political theory and its value in social
science as a process of model building. It also explicitly analyses the previous fictional
section according to certain minimal standards of logic, for example, the requirement of
linking means and ends coherently. Before exploring in some detail the social scientific
process of elaborating the criteria of utopian political theory qua theory, I will discuss
the nature and validity of utopian literature and its place in a particularly political context
using More and his Utopia as a primary example.
There have been two schools of thought about Mores Utopia from his
contemporaries to the present day that are generally instructive (Adams, 1975). One
school argues that the essential nature of Utopia is that of a joke, at best a satire
intended to demonstrate the absurdity of English customs of the period by a Most
Distinguished and Eloquent Author. The other school argues that it is indeed a serious
attempt by a man bent on creating a moral political order who presented the essential
elements of The Best State of a Commonwealth with calculated humor. It is difficult,
joke or ideal, not to take Utopia seriously at some level from a man who died at the
hand of his king challenging the morality of political life, if not the whole social order.
The good saint also demonstrated that lethal seriousness in his advocacy of the burning
of heretics as the church attempted to maintain a moral order.
Those two schools extend in scope beyond the controversy of Utopia to all utopias.
Is utopia a valid and important construct of our thinking and aspiration, or a bane to


clear thinking and planning that leaves only utopia-as-joke with any validity? And as a
sidebar, there is the whole realm of dystopia to consider, of utopia as the epitome of the
fold joke. Utopian literature intends to transcend reality; dystopian literature to gaze into
the crystal psyche of manunkind1 to delimit the fallout from the attempt
Generally speaking, three variations can be distinguished in the definitions
of the utopia. The first conceives the utopia as a particular literary style and
seeks the distinguishing characteristic of it in certain literary qualities. The
second calls the utopia a utopian, i.e., naive and prescientific, way of
thinking about society, for example, in The Development of Socialism from
Utopia to Science Engels seeks to distinguish an outdated and prescientific style
of Saint-Simon, Owen and others from the scientific socialism based in the
discovered laws of historic material development The third identifies utopia
with the critical approach to the form man has given to society. (Plattel, 1972,
pp. 41-43)
Bronowski in The Ascent of Man, expresses one of the distinguishing qualities of
human psychology, and perhaps the sine qua non, as the act of the vaulting athlete
whose behavior is driven not by the immediate environment, but by a set of goal-
directed assumptions lying not in the present but in the future (1973, p. 36). It is a
small leap to go from this distinguishing quality of human psychology and imagination
to the expression of those qualities through oral and written utopian constructs. From
this perspective it would be the expectation of a constant and unavoidable expression of
lupity this busy monster,manunkind, / not. Progress is a comfortable disease: /
your victim(death and life safely beyond) / plays with the bigness of his littleness /
electrons deify on razorblade / into a mountainrange;lenses extend / unwish through
curving wherewhen til unwish / returns on its unself / A world made / is not a world of
bompity poor flesh / and trees,poor stars and stones,but never this / fine specimen of
hypermagical / ultraomnipotence. We doctors know / a hopeless case iflisten:theres
a hell / of a good1 universe next door,lets go
pity this busy monster,manunkind, is reprinted from COMPLETE POEMS,
1913-1962, by E. E. Cummings, by permission of Liveright Publishing Corporation.
Copyright 1923,1925, 1931, 1935,1938, 1939, 1940, 1944, 1945, 1946, 1947,
1948, 1949, 1950, 1951, 1952, 1953, 1954, 1955, 1956, 1957, 1958, 1959, 1960,
1961,1962 by the Trustees for the E. E. Cummings Trust. Copyright 1961,1963,
1968 by Marion Morehouse Cummings.
28


utopian thinking as an integral part of humanity, rather than utopia as a particular event
or story by someone with an agenda. The critical intention to break through the
existing conditions and achieve a better future turn out to be the essence of the utopian
phenomenon (Plattel, 1972, p. 44).
The critical view of utopia, however, presents it as a symptom of a simmering
crisis, an expression of dissatisfaction with present circumstances and an imaginary
vision of different, more amiable ones. And the dystopians warn of the consequences
of such imaginative attempts toward change. Others declare that civilization is not an
aggregation of the civil individual but the repressive means for survival of death-
seeking beings. According to Freud, civilization is essentially restrictive and
repressive. With his pleasure principle man remains fundamentally an enemy of
civilization and its principle of reality (Plattel, 1972, p. 109). The resolution of that
contradiction lies in the old trick of moving to a more inclusive category where the
contradiction disappears, or at least appears in a greater context Utopia as a critique
and symptom of crisis does not exclude it as a normal and constant expression of
human psychology toward the future; it is a subset of it And the failure of the
scientific-socialist explanation of future reality lies not only in its many failures as a
i
predictive science, but also in its a priori assumptions and circular arguments where any
historical event can fit into the theory to prove it but not to disprove it.
Ideology or Transformation?
So we are left with utopia; utopia that this thesis accepts as serious. But is it a
utopia that vaults1 the present into future-oriented, non-existent circumstances, or a
utopia that is a not-so-subtle justification for present circumstances, unable to break free
of its material and social context? Karl Mannheim (1956) in Ideology and Utopia
29


I
analyzes the distinction between ideology and utopia. This distinction is used
analytically by Kerry Walters (1989) in The Sane Society Ideal in Modern Utopianism.
i
Basically, Walters argues that opposed to a utopia that breaks the barriers of status-quo
I
thinking as a prerequisite to social change, ideology, often disguised as utopia, presents
i
a picture of a rigid status quo in a propagandist fashion that justifies the state of current
I
ideas, classes, and institutions. Mannheim states,
every period in history has contained ideas transcending the existing order,
but theseldid not function as [nonideological ideas]; they were rather the
appropriate ideologies of this stage of existence .as long as they were
organically and harmoniously integrated into the worldview characteristic of
the period (i.e., did not offer revolutionary possibilities. As long [for instance]
as the clerically and feudally organized medieval order was able to locate its
paradise outside of society, in some other-worldly sphere which transcended
history and dulled its revolutionary edge, the idea of paradise was still an
integral part of [the elassbound ideology of] medieval society. (1956, p. 193)
Utopias on the other hand, are deliberate attempts to transcend both objective
reality and currently existing ideological structures (Walters, 1989, p. 67).
We have seen, following Mannheim, that utopian thought forms can be
distinguished from ideological ones on the basis of the difference in their social
functions! Ideologies tend to support the conventional, normative and
conceptual models operative in a given socio-economic context. As such, they
tend towards totalization, which in turn discourages social and conceptual
innovations and leads to a stagnation which eventually gives rise to alternative
utopian models. Utopias sense the tension between the putatively absolute
standards of ideological structures and actually existent socio-material
condition's and strive to alleviate it by introducing alternative worldviews and
social agenda. In doing so, they chip away at the ideological continuum,
thereby acting as vehicles for social and theoretical innovation. (Walters, 1989,
p. 72) ;
1 I
Here we can leave Walters thesis that the sane society ideal in modem utopian
I
novels such as Looking Backward are ideology, ignoring class realities and, accepting
Mannheims (1956) distinction between ideology and utopia, ask if the previous
30


chapters fictional Prospects vision is revolutionary or a redux of technology-based
industrial capitalism. The first criticism that could be posed is that the vision of the
prospects of information technology does not change in any fundamental way the
nature of mass industrial production and consumption, but only rigidifies it by
establishing a paradox where human liberation, freedoms, and equality totally become
dependent on a system of industrial, high-technology production and innovation,
requiring the resultant industrial structure of living/working and work discipline that is
by its very nature antithetical to freedom of choice. It could also be argued that such a
high-technology dependent political and economic system will either create a new or
sustain an old technocratic elite who will be able to wield an institutionalized form of
authority based on critical, specialized knowledge. This vision is little different than
Skinners (1948)Walden Two where a technocratic meritocracy will rise to power.
The difficulty with Walden Two, and many utopian visions is their static quality. It
is just that quality that is challenged the most by the Prospects vision. This is a dynamic
society where no long-term institutionalization of power nor crystallization of roles is
legitimate. The knowledge of information technology at the crux of the social, political,
and economic decision-making is not of a nature that can be buried in a backyard vault,
nor a single mind1. Yet the dissemination of such knowledge has to be planned, and the
nature of temporary and rotating responsibility would make elite-formation because of
this specialized knowledge very difficult.
In view of Mannheims (1956) distinctions, it is also evident that the Prospects
vision is not a totalizing vision, but rather one that fragments political and economic
society into voluntary aggregates who choose their own operating procedures through
democratic means. As for it presenting a basis for a strengthening of bourgeoisie
democratic-industrial forms, it is also evident that the basis of bourgeoisie class
31


I
exploitation, namely ownership and property, are devolved to a system of worker-
I
ownership, leases, and public/participatory disposition of wealth and power that would
preclude class formation and would leave it to critics to explain the functional or
material basis of such a class.
Establishing Means and Ends
The Prospects vision once distinguished as a utopian, not ideological, expression of
i
normative psychology (answering the question, what if) can then be subjected to a set
I
of criteria of utopia as political theory. Harold Rhodes in Utopia in American Political
i
Thought discusses the crisis in American social science at the end of the 1960s and
links it to the crisis of modem utopian dramas. In effect, Rhodes calls for a critical
i
linking of means and ends in political utopia and one that meets the standards of Robert
l
Lynd and George Catlin that Thus if the political scientist is to meet his responsibilities
i
according to the Lynd-Catlin criterion, he must (1) perceive a problematic condition, (2)
identify an alternative, and (3) specify a method for effecting that alternative (Rhodes,
i
1967, pp. 10-11). Rhodes, in attacking the paradigmatic view of political thinking
outside of scientific criteria, argues that the responsible social scientist can produce
theory that links appropriate means and ends according to methodological criteria.
Rhodes argues, and I accept the argument, that ought questions can be subjected to
investigation and! empirical verification and that the alternative of an inability of social
science investigation is the metaphysical slippery-slope of ought questions subject
I
only to human reason. Or, I would add, in light of Mannheims criteria, ought
questions then become ideology.
Problematic Condition. There are two problematic conditions that can be identified
in the Prospects vision. The first is the political tension between democratic
32


I
participation and the growing distance between state-enforced public policy and the
mass public. While arguments and research continue on the explanation for low voter
participation in American elections, the basic fact of decreasing participation in the
political structure remains; this at a time when the information available to decision-
makers and to the public as a whole has increased exponentially. And when the speed
with which the aggregation of voting has also increased significantly. This condition of
the body politic also remains a question of whose interests the state serves. In any
system dedicated to the proposition that all men are created equal can the state remain
i
a neutral embodiment of that principle, or will it always drift toward serving the
interests of one class above others? In his dystopian expose of revolutionary
development, Animal Farm, Orwell proposes that any revolution that establishes an
authority wielded by a minority will grow toward serving the interests of that minority
at the expense of] an increasingly alienated population.
If we accept the proposition that the ideal situation is one in which not only do no
harm but also do not allow harm is operative, have we then backed into a minimal
state that is morally justifiable as long as it protects the rights of individuals? Or as
Proudhon states,
To be GOVERNED is to be watched, inspected, spied upon, directed, law-
driven, numbered, regulated, enrolled, indoctrinated, preached at, controlled,
checked, lestimated, valued, censured, commanded, by creatures who have
i
neither the right nor the wisdom nor the virtue to do so_____It is, under pretext
of public utility, and in the name of the general interest, to be placed under
contribution, drilled, fleeced, exploited, monopolized, extorted from, squeezed,
hoaxed, robbed; then, at the slightest resistance, the first word of complaint, to
be repressed.. .That is government; that is justice; that is its morality. (Nozick,
1974, p. ill)
33


I
Whether the utopian vision is consistent with a minimal state or its antithesis is not
to be solved here, but as the crux of the problematic condition of the American polis it
is one of the driving forces behind the Prospects vision.
I
The second problematic condition is the tension between the political ideology of
American society and its economic ideology. It is a question that not only enters at the
production end, who owns and who decides, but also at the consumption end, what is
distributive justice, and is there an entitlement to certain economic goods and
conditions? This tension between worker and owner, the corporation as a legal
individual and real individuals as members of corporations, wage labor, the necessity
of continued economic growth, supply and demand functions, and so on, lead to
consequences of (exploitation, unemployment, alienation from personal economic wants
and needs, powerlessness, poverty, and a totalizing vision of one mode of living and
working requiring the discipline of hierarchy, imposed behavior, and over
consumption.
It is a condition that was explored in two issues of Utne Reader, a bimonthly
magazine of articles from the alternative press, in the following titles: Why Work?
When Theres So Much More to Life and Tor Love or Money Making a Living vs.
Making a Life. The person who works right up to self-destruction is often accorded
far more esteem that those seeking a more balanced life (Moody, 1988, p. 65). On
the other handor so they sayyoure free, and if you dont like your job you can
pursue happiness by starting a business of your very own, by becoming an
independent entrepreneur. But youre only as independent as your credit rating. And
to compete in the business community, youll find yourself having to treat others
your employeesas much like slaves as you can get away with (Ventura, 1991, p. 78).
34


This is the central expression of the contradiction between the powerless structure of
economic discipline and the life people seek to lead.
I
Identifying an alternative. The Prospects vision identifies anarchism as a positive
political theory, i.e., not the negation of the state, but rather the existing civil society
before the state justifies its existence. For example, Hobbes is aware that the state of
I
nature in which there is no organized society is a logical fiction; it is the basis for the
second fiction, the social contract (Carter, 1971, p. 15). And I would add that the
fiction of the state as a representative of the peoples will evolves quickly from the
social contract ideal. The difficulty with the anarchism ideal is that for there to be any
social decision-making there must be an aggregation of individual choices, which then
constitutes the peoples will, and at that point we must have some structured system
of aggregation and become susceptible to that systems physical and logical limitations.
The identified alternative, then, is the closest feasible approximation to a functioning
stateless anarchy.
Prospects also identifies a syndicalist type of worker-owner agricultural and
industrial production as an alternative. This would narrow the contradiction between
work and other aspects of living by allowing a wide range of voluntary organizations
whose benefits are to be reaped equitably. It also empowers everyone concerned with
production and consumption of the products of industry. This does not eliminate
difficulties and dissatisfactions, but gives responsibility to all and legitimizes that
decision-making. Factories will go out of business undoubtedly, but as a result of the
aggregated decisions of everyone, rather than a few. This system cannot eliminate risk,
only spread its share equitably.
The alternatives identified then are to eliminate the state and wield authority through
direct public and firm decision-making, and to devolve property to rights of use, not
35


ownership, and make all workers also owners at the level of the firm. The economic
I
vision differs from the political because microeconomic decisions need to be made at
the microeconomic level. The mass public has a diminishing investment in decisions
made in plants or on farms from which they do not consume nor prosper, and for
which they do not work.
Method for effecting the alternative. Here is the core of the thesis and of the
Prospects utopian vision, that in a mass, developed, industrialized society, information
technology provides the means for aggregating the kinds of complex choices needed
and implementing them with speed and accuracy, limited only by the logical limits of
the aggregating process. The negative of the thesis is simply that in the absence of this
technology there are no identifiable feasible and functioning means to achieve the
identified alternatives to the problematic conditions. This assumes that the
I
deinstitutionalization and disaggregation of current mass, developed culture is not
feasible, as demonstrated amply by the Chinese cultural revolution that failed not only
in its ends, but by its totalizing means became the antithesis of the alternatives presented
here.
The Place of Technology
What then of technology and its place in utopia? The products of the hand of
people, techne, ciannot finally be separated from mind. The division between science
and technology is the result of utilitarian thinking that science, or knowledge in general,
I
must have some application, some action, to have value. That analytical utilitarian
distinction itself has little value. Techne is always a product of the active mind; mind
i
and knowledge cannot be severed from their action on and in the world. In this sense,
no utopia can demonstrate a vision without a place for some level of technology, both
36


social and physical. Historically, there have been two main responses to the place of
technology in utopia, those that trumpet the wonder of technology and those that
trumpet its oppressiveness.
It is not until the seventeenth century that we find the beginnings of modem
exaltation of complex technology (Sibley, 1971, p. 17). In New Atlantis, Francis
Bacon expresses the profound faith of the progressive nature of science and technology
and the utopian future that a scientific society would have. This is the major vision of
industrial society as the conqueror of nature to carve out a human rational paradise
within irrational nature. It is a totalizing vision of technology as the liberator of the race
from original sin and its consequence, irrationality. Gone is the notion of limits to
what man can or ought to do with Nature. The idea of conquering Nature as an army
would conquer another nation makes its full-fledged appearance and will have an
enormous influence on the subsequent history of mens institutions and conceptions
(Sibley, p. 19). This view is intimately linked with the idea of progress as a linear,
additive, upward sloping process of attaining the perfect society. It is also intimately
linked with the capitalist industrial revolution and its ideal of unlimited material wealth
and unlimited expansion markets. In this genre, technology is not merely the means
toward a utopian Vision of society but the embodiment of that utopiatechnology is the
good.
The other response to technology in utopia has been [t]he despair of dystopian
writers about human capacity to control the technological process once it has been
initiated [leading] a few utopiasts in the last generation to formulate schemes which
either halt technology at rather primitive levels or selectively encourage some types
while prohibiting or restricting others (Sibley, 1971, p. 37). In A. T. Wrights
37


Islandia, a character defending the Islandian way of life expresses the view: Would it
be pleasanter if we had come by train from the City? (Sibley, p. 37).
This embodies the anti-technological paradigm presented by many utopian and
dystopian visions concerning not only the quality of experience that technology can
provide, but the dangers of technology out of control, as in Mary Shelleys
Frankenstein. Included in this genre are the dystopias antithetical to technology-as-the-
good where technology-becomes-the-bad leading to Orwells despairing conclusion of
1984 where the integrity of the individual no longer exists.
Human ambivalence about technology will remain in any utopian vision and the
Prospects vision uses the perspective called techno-structuralist, elaborated by
Tehranian (Tehranian, 1990, pp. 212-217). In this viewpoint, technologies are neither
good, bad, nor neutral in and of themselves. This is because they developed out of
institutional needs (in the case of information technologies, primarily military and
business needs) and their impact is always mediated through the institutional
arrangements and social forces... (Tehranian, p. 5). In other words, technologies
always feed into the social and institutional paradigm and have good, bad, and neutral
effects. It is the way that the paradigm uses and understands the technologies that will
determine the greatest share of effect of that technology. In this view technologies feed
into the institutionally created structures, magnifying strengths and weaknesses. The
Prospects vision takes three of the strengths of computerized information technology
speed, logic, and memoryto overcome limits imposed by the nature of society and
geography. It is the outcome of political will that will determine the characteristics of
the technology that prevails.
The overall conclusions of the chapter are that utopia, as a serious form of political
theory, must conform to certain criteria to have validity. Those criteria include, but are
38


not limited to, presenting transformative possibilities rather than ideology and
coherently linking means and ends. The Prospects vision presents information
technology as the central mechanism for meeting those requirements and I now focus
on that technology.
39


CHAPTER 4
THE TECHNOLOGICAL ANALYSIS
The Limits of Political Institutions
Chapter 4 looks at the place of information technologies in political structures.
Technology has its own internal logic and limits that must be explored both outside of
and in relation to the political structures it will serve, yet in a way that is non-
deterministic. And beyond limits and logic, it also explores technology as a process and
its possibilities of meeting the process needs of the Prospects vision.
It has been said that economics is the science of scarcity, as all the principles and
analyses that spring from the dismal science are based on an assumption of limitations,
limited resources, labor, capital, and land. In an analogous way political science is the
science of information and decision-making limitations and the power structures that
result There are several basic identifiable variables that enter into the portrait of political
limitations. One is population of the decision-making group. The number of members
of a political body will influence other variables, namely, the amount of land needed to
produce food, geographical distance between any two individual members and their
communities, family size and structure, ability to assemble and travel, time needed for
communication between members and communities, and types of aggregation/counting
mechanisms that can be used. All of these variables interact and affect one another on
one side of the equation, but on the other side is the resultant political system that must
live within the limitations of the variables as a whole to be feasible and functioning.
One of the most often cited examples of this qualitative equation is the limitation of
direct democracy in mass societies because of geographical and physical constraints.


You simply cannot cart off everyone in the society to a mass meeting, and if you could,
you wouldnt haye a large enough building to house them, nor enough time for
universal participation. This basic limitation of reality in economics is referred to as the
Production Possibilities Frontier (PPF), basically a zero-sum equation with two or
more variables. An increase in one, say production of televisions, necessarily leads to
decrease in another, artichokes, because capital, labor, and material are limited. Again,
we can create an ianalogous example in political science calling it the Institutional
Possibilities Frontier (EPF). You simply cannot create a feasible, functioning institution
that requires more personnel, information, or time than it has.
One of the exceptions of the limits in the PPF and the IPF is technology. A
restructuring of capital into a technology that uses the same labor and material more
efficiently can raise the PPF and IPF to new limits. It is important to point out that
limits are not eliminated, but simply redefined at a new level. An economy can perform
below the PPF Emits, but if maximum production is a valid good, then the situation is
not optimal. And again, a poEtical system can also perform below the IPF, but if
maximum participation and freedom of the individual are valid goods, then that
situation is also not optimal.
Overcoming Limits: Requirements for Democratic Technology
It is the contention of this thesis that while representative democracy may have
expressed the outermost Emits of the IPF at an historical point in time, that is no longer
the case. Technology, specifically, information technology, has pushed that IPF
outward and the current poEtical system is functioning suboptimaUy. Information
technologies provide the necessary means for a mass, developed society to meet,
41


I
discuss, and reach decisions with litde regard to geographical, transportation, or
population limitations. Tehranian (1990) states,
At the risk of oversimplification, however, let me conclude that information
technologies can in fact serve a more democratic world development on at least
the following three conditions: First, if they are made more interactive. Second,
if they achieve more universality and accessibility. And third, if they are
increasingly locked into participatory, democratic institutions and networks.
(P- 17) j
Some of the first steps toward interactivity have taken place on various scales in
several countries with television and cable.
The Qube system in Columbus, Ohio, was one such system that provided
interactive responses to viewers who were connected to a main computer at the
television station. Not only were preferences recruited directly but also time spent
watching television, channel choices, and so on, were recorded by the central
computer. The Qube system was instituted in several major cities in slightly different
formats. The systems offered entertainment, education, public opinion polling,
i
teleshopping, and community interaction. By 1984, however, Warner Amex, owner of
i
Qube, was asking to be released from its agreement under cable regulation. It wasnt
the technical infeasiblity of the system but rather a technology quickly out of date and
low community channel participation that led to heavy financial losses. (The
Economist, January 28,1984, p. 27, cited in Tehranian, 1990, p. 127)
The closest Qube seems to have come to .. .interactive social dialogue was
when in deference to its community obligations [under regulation agreement] it
offered channel facilities at no cost for town meetings.. .The Commission
asked a series of questions on which the citizens gave their preferences. Results
were displayed within seconds after they had pressed the buttons. To make sure
of the freedom that comes from anonymity of response, the Qube hosts assured
the respondents that the computer had been set in a mode that would not identify
them. Asked if they wanted to do the experiment again, 96 percent pressed the
Yes button, and within 10 seconds the computer, having worked out that
percentage, relayed it to the home screens. (Tehranian, 1990, p. 127)
42


The National Science Foundation also sponsored experiments in several U.S. cities
to explore possibilities of the mostly unused two-way interactive potentials of cable
television (CATV). A project in Reading, Pennsylvania, tested the audiovisual
conferencing for providing social service programs to the elderly. A Rockford, Illinois,
project applied CATV to in-service training for a single occupational group,
firefighters. And a Spartenburg, South Carolina, project offered formal education to
students in their homes. The initial findings were that, at least technically, all the
projects were technically feasible and functioned as projected. (Kaiser, Marko & Witte,
1977, pp. 16-23)
Such experiments have been conducted in many parts of the world, especially in
Japan, Europe generally, and (West) Germany. In Berlin, the Heinrich-Hertz-Institute
(HHI) provided interactive cable services to subscribers that included town planning,
social services, access to authorities, tele-education, purchases of goods and services,
j
and entertainment Such a contracted service, available in 1977, proves not only the
technical feasibility of such a system, but also its applicability. The HHI system is close
indeed to the system discussed in the Prospects vision, although the Prospects vision
|
downplays the entertainment and television potentials of such home/workstations.
The structure of the system tested relates directly to its function. An interactive two-
way cable system feeds into the centralizing character of computer information
technologies. Here, users can only interact with the center and receive information from
that center. This gives the power of information and control to the center and is only
made available from the center. This concept of dumb workstations dependent on a
central mainframe computer would not be ideal for creating a world like the Prospects
vision. Here, decentralized smart workstations that can communicate with a central
43


computer, or several central computers, and are also capable of point-to-point
i
communications with any other workstation, would be desirable.
i
One of the first political applications of computer information technology in the
U.S. was in urban government. Urban government can be viewed as an information
i
system in which data are collected, organized, stored, managed, analyzed, and
retrievedall ultimately for decision-making purposes (Westin, 1971, p. 331). The
application of computers in areas such as urban government in fact created fields of
study such as systems science and information management. While many had hoped
for a total system design iand implementation, as with most new technologies,
computers were integrated piecemeal and a great deal of information duplication and
confusion occurred. I think it is important to stress here that even with about 30 years
of integration of information technologies in the urban management area, no cities have
i
yet achieved an integrated and total systems operation. It is also important to note that
this use of information technologies so far has only served the bureaucracies and
i
l
officials already institutionalized by urban government; it has not served to open urban
government to the public, nor challenged the basic ways in which U.S. urban centers
I
do business. If anything, it has allowed urban centers to increase in population to the
size of many small countries and still maintain the established order. Some form of
computerized vote tallying has been implemented in almost every local voting precinct,
yet again the method of voting has changed little, only the speed and accuracy with
which the count has been performed.
We are an information automated and automating society. I do not think it is
oversimplification at this point to state that the integration of information technologies to
date has tended to feed into the current institutional political and economic framework
by strengthening, rather than challenging it. The most trivial use yet put to computers
44


I
I
has been in homes where they remain isolated devices with programs to store recipes
and addresses or produce computerized entertainment But the important question does
not concern critique but why this this so. Part of the answer lies in the ideologies of
technology that are presented. [T]echnophiles tend to be the optimists who believe that
the present technological revolution in information storage, processing, and retrieval
has already inaugurated a post-industrial, information society with higher productivity
and plenty at the world centers that will eventually trickle down to the peripheries
(Tehranian, 199Q, p. 4). According to this view, information technologies have already
done what they do best, by making present systems more efficient. Returning to
Mannheim, even though most of these portraits of future techno-society couldnt be
classified as utopian, the future they portray has little revolutionary potential. The
technologies have deterministic qualities and not surprisingly those qualities tend to be
the capitalist/industrial and representative democratic ones already in existence. This is
ideology.
Another perspective that tends to feed into the present institutional framework is the
techno-neutrals... who have few theoretical pretensions and considerable interest at
stake not to alienate their clients (Tehranian, 1990, p. 5). These are the consultants and
engineers who design according to the needs of the institutions they serve. This is also
a reflection of the corporatist employee status of most engineers and information
processors. The institutions they work for do not demand nor desire revolutionary
ideas. This non-ideology is also ideological according to Mannheims (1956) analysis
because it also serves the interests of the classes and structure as they exist.
The answer also revolves around economic structures. The Prospects vision society
would require an enormous capital investment in information technology to meet the
second requirement of Tehranian that they be made universal and accessible. The
45


revolutionary democratic potential in the workplace and society is a damper to most
current institutions to invest in such a large capitalization project They may be putting
I
themselves out of business and restructuring social and economic power in
unpredictable and uncertain ways.
Most capital is controlled by corporations or by governmental units through
taxation. As discussed above, urban governments have defined the public good as an
investment in information technologies that will make their functions easier and more
efficient, not a decentralization of power to direct voting. Analogously, corporations
have not seen information technologies as a worker empowerment tool, but one that
could make them more efficient The first application of multimillion dollar, room-sized
computers that could do little more than hand-held calculators today was accounting and
payroll. The efficiency of billing and ordering represented an enormous long-term
savings and increased earnings for the corporation. Who will pay? It will have to be
individuals who are invested politically and economically in universal and accessible
information technology.
The third requirement of Tehranian is that information technologies be locked into
participatory, democratic institutions and networks. Two examples of experiments in
the participatory vein are televoting ... a novel method of public opinion polling
originally designed by Vincent Campbell as a new public communication system for the
San Jose Unified School District in California (Tehranian, 1990, p.112).
In 1978, Ted Becker, Richard Chadwick, and Christa Slaton of the
University of Hawaii revised the San Jose Televote in order to turn it into a
scientific jrandom public opinion sample of a population. In contrast to
conventional public opinion polls, however, the new Televote method attempts
to inform the public before sampling their opinions. Following a random
selection of Televoters, they were provided with brochures on the issues at
stake. Ample time is allowed for the reading of these materials before the
46


I
Televote staff calls up the voters to ask for their responses. (Tehranian, 1990,
p. 112)
A New Zealand televote in 1981 also surveyed a sample population on the future of
New Zealand and encouraged televoters to make some difficult choices among four
different futures for their country. (Tehranian, 1990) While televoting is another
example of the application of information technology, it was basically implemented as
another method of random-sample polling on certain questions, which of course suffer
from the same biases as any survey. Also, the televoting is center-to-point, not point-
to-point, so that the bias comes directly from those at the center and cannot be
overcome by point-to-point debate and communication. The voter doesnt set the
i
agenda. Paul Goodman spoke to this question of the place of technology on that
Institution Possibilities Frontier discussed above in Can Technology Be Humane?
I need hardly point out that American society is peculiarly liable to the
corruption of inauthenticity, busily producing phony products. It lives by public
relations, abstract ideals, front politics, show-business communications,
mandarin credentials. It is preeminently over technologized. And computer
technologists especially suffer for the euphoria of being in a new and rapidly
expanding field. It is so astonishing that the robot can do the job at all or seem
to do it, that it is easy to blink at the fact that he is doing it badly or isnt really
doing quite that job. (Teich, 1990, p. 243)
i
If the televote is just an extension of opinion polling and the technology is really
doing a poor job compared to its potential, then what are the possibilities? Tehranian
discusses how
... information technologies, no matter how interactive, cheap, or
accessible, do not by themselves lead to democratic formations. The latest
[1984] U.S. census data demonstrates the point well. (1990, p. 236).. .the
Bureau of the Census has confirmed the suspicions about a widening gap
between information-rich and information-poor. According to this report based
on a survey conducted in 1984, some 15 million American adults had
computers at home, but only 53 percent used them. Predictably, the figures
also suggest the creation of a computer elite based on race, sex, and income.
47


Only about 3.4% of children in households with annual incomes of less than
$10,000 had a computer at home, compared with 37% of children in families
with incomes of $50,000. Of those who had them, boys were more likely to
use a computer than girls (80% to 66%), and among adults 63% of men used
computers at home compared with only 43% of women. As for race, 17% of all
white children used computers at home, compared with 6% and less than 5% of
black and Hispanic children, respectively. (The Economist, April 23,1988,
cited in Tehranian, 1990, p.156)
In contrast to privately owned or govemmentally operated information media
systems, Tehranian discusses several characteristics of what he would consider a
I
communitarian system, all of which I believe are evident in the Prospects vision. They
are community ownership and management, deprofessionalization of programming and
production, empowerment of audiences, interactive technologies and networks,
decentralization, cultural and structural pluralism, and thinking globally, acting locally.
The implementation of the Prospects vision would not come about because of some
j
deterministic quality of information technologies. It would not become a dystopia
through those same qualities, but rather would be implemented through the political and
economic struggle of those who would want to restructure institutions to take advantage
of the speed, logic, and memory capacity of information technologies to expand the IPF
to include mass, developed anarcho-syndicalist forms.
The Logic of the System
Having analyzed the place of information technologies in a political context, I now
turn to the limits of the speed, logic, and memory capacity of information technologies
themselves and the boundaries that creates for the design of institutions. The Baconian
1 i
i
view of progressive science as a limitless enterprise of gathering knowledge to eternally
better the human condition was probably most symbolically overturned by the dramatic
logic and subsequent experimental verification of Heisenburgs uncertainty principle in
48


physics. (Heisenburg's uncetainty principle is a mathematical relation that demonstrates
that if an experimenter locates the exact position of a subatomic particle, the speed
cannot be calculated exactly; and conversely that if speed is determined exactly, then
location can only be estimated. This is not a limitation of the experimental apparatus,
but a limit imposed by nature.) That the very reality that had so cheerfully given its
secrets to the scientific method would also impose ultimate limits to knowledge pulled
the foundation from progressive natural science. In a similar way, Arrows
impossibility theorem within the context of general social choice theory pulled the
foundation from under progressive social science which held that once you specified a
set of preferred criteria for the good society, only implementation remained. Arrow
specified a set of desirable and consistent conditions and discovered, It is not just that
it is difficult to find a social choice rule that satisfies all these_No, it isnt just that it
is hard; it is impossible (Kelly, 1988, p. 80).
The tension is between the individual and aggregation of individual preferences
(wants and needs) into social decision. This can also be complicated infinitely by
unanimous subsets of individuals aggregating subset preferences into society. To
maintain some simplicity, I will assume only the tension between the individual and the
aggregation of preferences and its application in the Prospects vision. Society then is
merely the aggregation of individual preferences into some form of communal action.
The crux for the information engineer, according to Arrow's (1970) theorem, is that
there is no software program, no technological breakthrough that can overcome the
logical limits of the non-existence of a social choice rule that will simultaneously satisfy
all the desirable conditions of a social system.
The principle tenet of social choice theory and economics from which it sprang is
the assumption of a rational actor and rational choice. Certainly many fundamental
49


social science constructs can be attacked at this foundation level by denying (subject to
proof) that in fact that assumption is untenable. For the purposes of this thesis I dont
believe there need be any further exploration of this question. The actor can be rational
or irrational as can the social outputs resulting. My primary concern is with the means
of aggregate choice, and that means must always conform to some rational structure. In
fact it is more applicable in the realm of information technology and social choice
programming, because those must be expressed in rational structures that can be
processed with technology that conforms to its own rational limits, e.g., at present the
limits of binary information coding.
The first of the resulting analyses of democratic forms based on the rational
assumption is the contradictions of majority rule. Arrow states, When I first studied
the problem and developed the contradictions in the majority rule system, I was sure
that this was no original discovery (1970, p. 93). In fact, this had been discussed
historically by Condorcet, Borda, Laplace, Nanson, Galton, and others. The simplest
explanation of this problem is that ... there is not a unique way of extending simple
majority voting to make decisions among three or more alternatives (Kelly, 1988, p.
15). For example, three people voting on three possible alternatives (x, y, z) can end in
a situation where their preferences are ordered as the following:
1: xyz
2: yzx
3: zxy
In this situation, if we aggregate by Condorcet winning pairs, on the first count x is
preferable to y (no. 1 and no. 3 would prefer x to y); on the second count y beats z (no.
1 and no. 2 prefer y to z); and on the third count z beats x (no. 2 and no. 3 prefer z to
x). In other words there is no winner with this vote of preference ordering. This
method for aggregating individual preferences among three individuals with three
50


alternatives can lead to a situation where the logic of the system produces no aggregate
decision even though each individual is clear in preference. And Arrows impossibility
theorem tells us that there is no system with a set of conditions that can aggregate
individual preferences into a social choice meeting all the conditions. This doesnt mean
that there are no methods for getting around this difficulty in the system, only that the
difficulty will always remain. How then are democratic systems to be designed to
confront these aggregation limits?
A second related question also needs to be asked. What if the system does work
and there is a majority victor? What are the consequences for majority rule? If one of
the conditions (as it is in Arrows theorem) is that there be no dictator (and in this thesis
more generally, no wielder of authority) can the majority act as a dictator? It is a long
and well debated idea that in direct democracies the majority can treat the minority
tyrannically. As I argued... the principle of majority rule entails, at the very least,
that if one of a set of feasible alternatives is the first choice of a majority of voters, then
that alternative ought to be chosen (Sugden, 1981, p. 176). Majority rule is certainly
the key procedural attribute of a democratic system, but it does not follow that where
there is majority! rule there is democracy. First, it is evident from the contradictions of
majority rule that there are instances where the system simply exceeds its logical limits
and cannot produce a social preference aggregate that also corresponds to the
preferences of the individuals who voted. Second, there are circumstances where the
above rule expressed in Sugden if there is a majority, the first choice of that majority
prevails as the aggregate of the individual preferences simply is not the will of the
majority. And it is this moral claim that a majority expresses an aggregate social will
that gives democracy its political force. For example,
51


A community of 1000 people is made up of two villages, A and B, which
are several miles apart The question at issue is whether licences should be
given to allow [pubs] to be set up. A majority of the 600 inhabitants of village A
are drinkers; in village B, a majority of the 400 inhabitants are abstainers.
Drinkers are in favour of pubs while abstainers object to the associated noise
and traffic. There are four alternatives: that pubs should be licensed in both
villages (w), that a pub should be allowed in village A but not in B (x), that a
pub should be allowed in village B but not in village A (y), and that no pubs
should be allowed in either village (z). The profile of preferences is: 1-450:
(w,x,y,z); 451-600: (z,y,x,w); 601-750: (w,y,x,z); 751-1000: (z,x,y,w).
Voters 1-600 live in village A and the rest live in village B. Alternative w, that
pubs should be allowed in both villages, is the first choice of a majority of the
whole community. (Sugden, 1981, p. 177)
In this example, a pub, to which a majority of residents of B object for their village,
is imposed by a majority of overall aggregated voters. There are also other examples of
alternative methods to just simple majority rule, e.g., qualified majorities, log-rolling.
But I dont want to stray too far from the main point, which is the question of whether
the Prospects vision is simply another form of expanded representative democracy with
the majority a tyrannical wielder of power and authority rather than the representative
state machinery. One way out of the morass is the way pointed by what Arrow (1970)
calls extended sympathy and in the context of justice by Rawls. That is essentially to
be able to put yourself in someone elses shoes or blind institutional roles. How
would individuals act, and how would it affect the preference ordering, if they did not
know what institutional role they would fill. It is exemplified, in perhaps an extreme
form, by an inscription supposedly found in an English graveyard. Here lies Martin
Engelbrodde, / Hae mercy on my soul, Lord God, / As I would do were I Lord God, /
And Thou wert Martin Englebrodde (Arrow, 1970, p. 114).
This is the case in the Prospects vision where the aggregation of individual
preferences is through a diverse system of smaller voluntary units whose aggregating
I
i
systems vary, rather than through a totalizing single system of aggregation. For
52


example, the jury in the Prospects case was chosen by random selection as was the
second presenter; the first presenter volunteered based on merit and was accepted by the
case committee that the city had formed. The judge was chosen by community election,
and the whole process was overseen by all the individuals who had immediate and real-
time and also later-time access to the case. The lack of a totalizing system does not
guarantee that the limits of aggregation will not appear in some failure to match the
aggregate to individual preference, but it does guarantee that that limitation will not
appear because of a totalizing system. The potential for consensus exists because
workstations are point-to-point and preferences can be changed, rather than simply
counted.
When would consensus be an adequate substitute for authority? An
organization whose members have identical interests and identical information
will be one in which spontaneous consensus would be efficient; each member
would correctly perceive the best decision according to his interests, and since
the interests are in common, they would all agree on the decision. In face-to-
face groups, it may be possible to interchange information cheaply enough
[italics added] so that the identity of information can be achieved, and if the
group has a sufficiently overriding commonly valued purpose, the identity of
interests may also be a valid assumption. (Arrow,1974, pp. 69-70)2
The final sanction on majority tyranny, however, is the legitimization of the
secession of individuals from any system. While that is true of every political system,
usually called revolution, the cost for secession is usually so high that suboptimal
functioning is often preferable. On the other side, concerning the lack of stability and
opportunity cost of constant change, there are also simple physical limits to the number
of secessions an individual can withstand, whether there is an external authority or not.
21 would extend' this definition of face-to-face groups due to the technological
expansion of the geography/information limits discussed on page 38.
53


The Prospects vision also works because the extended sympathy requirement can
be met by random selection for the short-term institutional roles necessary for
functioning. Why would a person act justly, according to Rawlsian analysis, when it is
only a moral question? Make that moral question a reality, however, by randomly
choosing roles and the justice is evident (Not that this would guarantee that an
individual would act justly in that role, only that this is the best way to make the
attempt)
Authority and Individual Choice
I am left with two central questions to explore, the problem of authority in the
Prospects vision expressed by the court judgment and does random authority have any
greater moral claim than institutionalized authority. The problem of authority in the
Prospects case was expressed by the defendant character, Sharon, By your own
beliefs how can you enforce such a judgment, a verdict? How can you justify the
coercive intrusion into my life and welfare and how will you enforce it except by
physical force? ... For you will have to destroy your society to enslave me and control
my actions and words... You will end non-authoritarianism and the lack of a state
i
with me, or I will do it for you. Can the court assume a position of authority and
enforce its decision for the lifetime of the defendant without destroying the anarchistic
society of radical equality it values? Radical equality does not eliminate the human
condition of authority arising in any cooperative effort. What it does presume is that
authority will be shared and equitable and will not crystalize into status quo institutional
forms where individuals attached to certain roles become constant over time. If all
individuals have 'the same opportunity and responsibility to wield social authority over
time, personal authority and freedom can be maintained while the social authority is
54


shared equitably. The intrusion into the defendants life is justifiable because to do so
retains the equitable form of power distribution, whereas a lack of intrusion solidifies
the absolute authoritative claim of the defendant over that equitable distribution.
Does randomly distributed authority have any greater moral claim than
institutionalized authority? Smith and Ricardo both demonstrated the superiority of
specialization, and how, through trading specialized goods at certain rates of exchange,
both parties ended up gaining in valued goods. Apply this analysis to the political
function of wielding authority. Can two or more individuals be better off by
specializing, some in wielding authority, some in yielding it, than both individuals
retaining rights to authority?
A more technical and complete restatement is useful. The generalized
Hobbes argument [that in the absence of authority, there is a war of each
against all, and as a result, the life of man is poor, nasty, brutish, and short.]
presupposes two elements: the superior productivity and complexity of joint
production, and the cost of interchanging information. (Arrow, 1974, p 56)
In the Prospects vision the capital investment has been made and the cost of
interchanging information lowered to the point that the authority argument is negligible.
The question then remains whether the ceding of an individuals (x) authority to another
individual or grotip (y) would result in superior productivity and a protection of all
individuals greater than if they operated separately. If so, the rational individual would
prefer to cede personal authority to others to receive a net benefit
This argument assumes that it is a rational choice that is available. It is also a result
of speculation about the arising of unequal authority in the form of institutions and the
state. This is the importance of the myth of the social contract It assumes that because
there is unequal authority and the institution of the state exists that rational individuals
have signed the Social contract and found a net benefit in doing so. But where is an
55


individual to be found who has signed the contract? Where is the person hiding? In
fact, we are all socialized into the political systems of power and authority without ever
being asked to rationally evaluate and sign-on. What of an individual who wishes to
sign-off the social contract? The person is no less subject to the political system of
power and authority than before and often also loses personal freedom. Thus the state,
and systems of authority, as we are socialized into them are coercive. There is no
rational choice in fact, only revolution.
A rational individual then, it is my contention, would find a system of random,
equitable authority where the social contract was a real device and could be signed-on
or signed-off to have a higher moral claim than a system of institutionalized authority
where no such rational choice is possible. If the institution were non-coercive and
allowed individuals to sign-off, then I would argue that the rational individual would
be indifferent to the two systems because individual authority would be retained under
either. The non-coercive state is more of a perfected vision of utopia, requiring
assumptions of the perfectibility of human beings, than the Prospects vision, requiring
no such assumption. The polar alternative to authority would be consensus______By
consensus I understand any reasonable and acceptable means of aggregating individual
interests (Arrow, 1974, p. 69).
.. .some of us who have read a little bit of the history of thought have
heard of anarcho-syndicalism before. Bakunin and Sorel had spoken to the
same point many years ago. But it is a real one. There is a demand for what
might be, termed sincerity, for a complete unity between the individual and the
social roles ... (Arrow, 1974, pp. 15-16)
i
This chapter has focused on the limits and potential of information technology in the
Prospects vision as both transforming and functional. The argument that is presented is
that at a minimal level, where no transformation of systems take place but only novel
I
56


forms of process in the same system the Prospects vision still increases the level of
individual freedom through non-coercive participation. The question that remains is
what model of transformation would best serve maximizing individual freedom with
technology as the process means.
I
57


CHAPTER 5
THE ANARCHO-SYNDICALIST FOUNDATION
The Anarchist Vision
Chapter 5 explores anarcho-syndicalism as an appropriate utopian model made
functional and feasible through information technology processing. The historical
difficulties of the model are presented and questions central to it, authority, property,
and non-coercive decision making, are presented.
The first difficulty in discussing anarchism in general is that there are many
anarchisms. Like the many socialisms that were part of the international movement,
anarchist thought has produced collective, radical individual, peasant, pacifist, violent,
communist, conspiratorial, and many additional minor versions of theoretical and
activist ways to the stateless, cooperative society. Unlike socialism, anarchism has not
undergone an analogous open debate and, frankly, open warfare to distill the theory
into what is workable or winnable. There are also very few models of anarchist
development, of how in the real world anarchist societies can confront the day-to-day
concerns and decision-making of a community. This strikes both ways. Anarchism as a
critique is powerful because of its theoretical diversity and purity from problems of
application. But that same lack of application and historical precedent often gives the
i
critique little validity. The many anarchisms share the quality that there is no
institutional means of coercive enforcement of authority; that does not mean that there is
no social order or organization.
I want to be clear on a point. There are numerous examples of anarchist or
anarchist-style communities and cooperative efforts. Michael Taylor in Community,


Anarchy and Liberty (1982) discusses anthropologically-based descriptions of
anarchistic communities that include acephalous societies, centralized redistribution
systems, and chiefdoms and big-man systems. Acephalous societies (literally, no head)
have almost no political or economic specialization and what does exist is ad hoc
concentration of authority that flows continuously throughout the membership.
I
Centralized redistribution systems have crystalized authority around various hereditary
or divinely sanctioned leaderships, but that authority is under obligation to be used for
the benefit of all (usually in the form of provision of large feasts). Non-leaders have
more claims on leaders by virtue of their position than is true of the reverse. Chiefdoms
and big-man systems have considerable inequality of prestige and authority which again
in large measure, depends on merit and generosity. Taylor includes peasant and
intentional communities as examples of anarchistic organization as well. The critical
attribute shared by all these systems that Taylor presents is that they have no formal,
legitimate means of enforcing what functional authority they may have. That authority
is always in fluxin effect, there is no state.
The theoretical exploration of the state arising as in Hobbes work resorts to
speculations on the state of nature, a state that transparently did not exist, or if it did
was extraordinarily short lived because of undesirability of the war of each against
all. This view assumes the continuity of the state form of coerced social welfare from
time immemorial and ignores the very process of the state arising from non-state
communities that it purports to explain. During almost all of the time since Homo
sapiens emerged, he has lived in stateless, primitive communities (Taylor, 1982, p.
33). The Kung! of the Kalihari have in fact maintained such societies up to modem
times. The difficulty is not in the existence of feasible, functioning anarchist societies
but their scale. The crucial question is can this form of organization exist in mass,
59


developed societies? Authority embodied in the political state and the economic
authority of a society is the issue surrounding that question.
We are communists. But our communism is not that of the authoritarian
school: it is anarchist communism, communism without government, free
communism. It is a synthesis of the two chief aims pursued by humanity since
the dawn of historyeconomic freedom and political freedom... The means
of production and of satisfaction of all needs of society have been created by the
common efforts of all, must be at the disposal of all. (Dolgoff, 1974, p. 29)
The Syndicalist Vision
The economic authority is ignored or dealt with cursorily in many of the anarchist
perspectives. Some perspectives, for example, peasant anarchism that idealized the life
of the European peasant advocating withdrawal from the state to mutualist agricultural
societies, are simply inappropriate for exploring the place of anarchist ideas in mass,
developed society. For this reason, and because syndicalist organization at the level of
the firm can potentially deal with contradictions between micro- and macroeconomic
decision-making, anarcho-syndicalism makes the most sense as a vision of liberated
mass, developed society.
.. .the anarchism practiced and preached by a radical trade unionism
proved of a sounder variety. It was first and foremost based on the realities of
nineteenth century European life; and drew its support from the struggles
between classes that was at the center of the historic drama. As one writer put it:
Anarcho-syndicalism is par excellence the fighting doctrine of the organized
working class, in which the spirit of enterprise and initiative, physical courage
and the taste for responsibility have always been highly esteemed. (Horowitz,
1964, p. 35)
Syndicalism in the form of worker-owned and operated firms is no mere theoretical
construct Numerous variations on this theme provide models for approaching
empirical questions of how such firms operate, and how they can be constructed to be
60


efficient and competitive. Examples of long-term, successful worker-owned firms
include Plywood Co-ops in the U.S. Northwest, Mondragon in Spain, the socialist
worker-managed industries in Yugoslavia, and many smaller and diverse, yet no less
important, firms across the globe (Zwerdling, 1984). But the anarcho-syndicalist
version of worker agitation and control was less clearly successful.
The theoretical expansion of anarcho-syndicalism from a narrow class-based tool,
the fighting doctrine of the organized working class to a direct economic and political
struggle to liberate mankind from the state by Fernand Pelloutier and others, makes of it
an appropriate critique of the state and institutionalized authority, not just another
analysis of class-based political theory. Yet a renewed use of anarcho-syndicalist theory
in this thesis requires some speculation and addressing of the historical reasons for
anarcho-syndicalist failure. Horowitz in The Anarchists (1964) identifies three
problems: 1) They tended to approach socialism as a reality around the comer, rather
than a long-range process of social reorganization. (Lack of principles or program.) 2)
They abandoned the task of organization. 3) They failed to offer sound sociological or
psychological reasons for getting people to act. It failed to distinguish between the ends
of action and the stimuli to action. I would add that they also lacked the technical means
for organizing the society envisioned in the absence of the state.
Engels in his On Authority criticizes the anti-authoritarians strongly on the
grounds that they assume the new society is about to be bom, full-grown, like Minerva
from the head of Zeus. Authority, Engels argues, is just what the new society needs
(Marx, Lenin, & Engels, 1974, pp. 100-104). What Engels fails to realize in his
critique is that the anti-authoritarians or anarchists of which he speaks are criticizing
the principle of authority on the same basis, namely that a revolution that maintains the
state principle of authority gives birth to another state bom, full-grown from the head of
61


the old. How then can anarcho-syndicalism develop a program and principles? The
moral imperative is the historic drive toward freedom and equality; it is not rational for
an individual to choose less autonomy than human capacity allows, and even if an
irrational individual did make that choice, there is no imperative other than coercion
preventing a reversal of that choice. The fairness imperative is the opportunity cost of
coercion, a cost that has become clear in one arena through the arms race and vast sums
of money spent on standing armies across the world. The practical imperative is the
continual and long-standing abuses of life and liberty that states act out from political
detention to the holocausts of millions. These principles become program when a
I
means is provided to achieve the anarcho-syndicalist vision, a program that includes
feasible, functioning worker-owned and managed firms, expanded use of direct
democratic forms (initiative and petition) toward anarcho-syndicalist aims, application
of technology to information gathering and decision-making, passive resistance to state
authority, and so on. Horowitzs first cause of the collapse of anarcho-syndicalism
historically does not imply that there can be no program or principles as this example
hopefully illustrates.
Secondly, the task of organization is one that must occur through the active
integration of means to ends. This is Horowitzs weakest point because the anarcho-
syndicalists did not believe they had to organize because historical development would
lead their direction. To say that anarcho-sydicalists failed to organize because they
didnt organize is a bit redundant. Yet, I accept Horowitzs point that the failure was
not in their lack of organization but their belief in the inevitability of historical
development
Thirdly, there is more than enough stimuli to action to analyze since the writings
of most anarchists around the time of the French Revolution. The modem technological
62


state has used coercive and destructive force on scales unimaginable to monarchs and
radicals alike. The struggle to constrain state power in the twentieth century has taken
an international statist form, however, in the United Nations and other international
security organizations, rather than in a restructuring or abolition of the state itself.
And, finally, the means for mass point-to-point communication and mass
aggregation of individual preferences is available and technically feasible. A liberated
society, I believe, will not want to negate technology precisely because it is liberated
and can strike a balance (Bookchin, 1971, p. 134).
I do not wish to belittle the fact that behind a single yard of high quality
electric wiring lies a copper mine, the machinery needed to operate it, a plant for
producing insulating material, a copper smelting and shaping complex, a
transportation system for distributing the wiringand behind each of these
complexes other mines, plants, machine shops and so forth.. .let us grant that
copper will fall within the sizeable category of material that can be furnished
only be a nationwide system of distribution... This distribution system need
not require the mediation of centralized bureaucratic institutions. (Bookchin, pp.
137-138)
Property and Law
The mediation necessary in place of centralized bureaucratic institutions that wield
coercive authority is provided for precisely by the anarcho-syndicalist vision.
What of property in that vision? The analysis of the origins of property and the
origins of the legitimacy of property by many political philosophers is usually rooted in
the same state of nature fiction as the social contract and the arising state. The
difficulty with such an analysis is that the individualist definition of property (as land
staked out and mixed with labor for survival resulting in a legitimate property claim)
does not correspond with the world into which we are bom. Here there is no unclaimed
land, no stakes left to put down, and a system of state sanctioned property rights that
63


extend far beyond survival needs. Property is a legal claim on capital, land, and labor
that can be obtained, extended, voided, and created by other legal meanswith the
state as the coercive authority to back the claim. Proudhon claims in Property and
Revolution that It is robbery... Such an author teaches that property is a civil right,
bom of occupation and sanctioned by law; another maintains that it is a natural right
originating in labor.. .1 contend that neither labor nor occupation, nor law, can create
property; that it is an effect without a cause (Horowitz, 1964, p. 87). He also
discusses in The General Idea of the Revolution in the Nineteenth Century that
The people, even those who are Socialists, whatever they may say, want to
be owners; and, if I may offer myself as a witness, I can say that, after ten
years of careful examination, I find the feelings of the masses on this point
stronger and more resistant than on any other question. I have succeeded in
shaking their opinions, but have made no impression on their sentiments___
that the more ground the principles of democracy have gained, the more I have
seen the working classes, both in the city and country, interpret these principles
favorably to individual ownership. (Proudhon, 1969, p. 210)
Property, or ownership, in this version differs from the legal entity by being based
on personal use,! rather than speculation. The state simultaneously sanctions certain
forms of speculative property claims, when it strengthens its authority interests, and
outlaws other forms when it threatens those interests. Proudhons basic conclusion for
the use and disposition of property and social goods is by contract rather than law.
Rather than tangentially explore the idea of non-state contracts as legitimate where law
is not and its relation to property ownership, I will simply reflect that the Prospects
i
vision makes use of this idea of individuals voluntarily entering into community
contracts that decide the disposition of property within those communities. That
disposition could vary from community to community. It is assumed that under these
conditions the disposition of grandiose speculative property claims would not be in the
64


best interests of the individuals of the community and would not arise without the
authority of the state to enforce those claims.
The complaint is then often raisedwhat of monopolies? price fixing? cornering
the market? Are these not legitimate limitations on the free market that without state
authority would develop out of control? Here we must remember that what the state is
controlling is its own creation, namely the legal entity of the corporation with
recognized rights; and duties that the state uses its coercive authority to protect
Monopolies and price fixing are the products of the state and its corporate creations, not
the free market.
Non-coercive Social Decisions
I
The tragedy1 of the commons probably best describes the free-market concern
between public welfare, the commons, and individual rational self-interest. The
argument is set out by Garrett Hardin: A pasture is open to all. The village shepherds
keep animals on the commons and each is assumed to be maximizing his or her own
gain. As long as the common pasture capacity can handle the number of grazing
animals, a shepherd can add an extra animal without affecting the yield of his animals,
others animals, or the sustainability of the common pasture. However, at that limit the
shepherd will have a gain and a loss from adding one animal. However, the net benefit
of added milk, meat, etc., accrues to the shepherd while the loss is spread over all the
shepherds. In this situation it would be rational for the shepherd to continue adding
animals, as net gains would continue to accrue, and the shepherds collectively, all
acting in their best self interest, could destroy the ability of the pasture to support
livestock at all.
Abstracted, this problem becomes a game known as the Prisoners Dilemma found
in Games and Decisions by R. Duncan Luce and Howard Raiffa and reiterated in the
65


political context by Michael Taylor in Anarchy and Cooperation (1976). Two
individuals have a choice of two courses of action. The two individuals must choose
their strategies at the same time, or in complete ignorance of the others choice.
Associated with each pair of choices is a payoff based on four variables all of which are
related with decreasing value. Graphically, this would appear as the following matrix:
Individual 2
C D
C
D
where y>x>w>zj rows are chosen by individual 1 and columns by 2, and the first entry
in each cell of the matrix is the payoff to 1, the second to 2. Each player would obtain a
higher payoff if he chooses D (Defect) rather than C (Cooperate), no matter what the
other player chooses. However, by choosing D, each player gets a payoff w. A choice
I
for strategy C would have yielded each player a payoff x, where x>w. We define a
Pareto-optimal outcome as one where no other outcome is strictly preferred by at least
one player. An outcome that is not Pareto-optimal is Pareto-inferior. The dilemma is, of
course, that the rational choice for maximizing individual welfare (getting payoff y),
leads to a Pareto-inferior outcome for both players together. Rational individual choice
cannot be aggregated into mutual welfare in this game. Even if the individuals could
communicate, there is no incentive to keep the agreement because defecting from the
agreement would lead to a higher individual payoff.
Taylor takes the simple static Prisoners Dilemma and makes it dynamic by adding
the time element and allowing a number of iterations of the simple game. He terms this
the Prisoners Dilemma Supergame. My purpose in restating Taylors analysis here is
not to reproduce his argument in all its mathematical and logical complexity, but rather
x, x z,y
y, z w,w
rH
1
66


to look at his conclusions based on this analysis. The tragedy of the commons and
the Prisoner status of the game players is that a rational individual making rational
maximizing choices when aggregated with other rational individuals leads to Pareto-
inferior outcomes. This is certainly one of the basic arguments of modem state theorists
for the justification of the state as a welfare maximizer. Hume, for example, argues,
Two neighbors may agree to drain a meadow, which they possess in
common; because tis easy for them to know each others mind; and each must
perceive, that the immediate consequence of his failing in his part, is the
abandoning the whole project. But tis very difficult, and indeed impossible,
that a thousand persons shoud agree in any such action; it being difficult for
them to concert so complicated a design, and still more difficult for them to
execute it; while each seeks a pretext to free himself of the trouble and expence
[sic], and woud lay the whole burden on others. (Hume, 1888, p. 538)
Taylors critique of this view involves the results of his Prisoners Dilemma
Supergame where a number of strategy outcomes can lead to Pareto-optimal results.
There are also many strategy vectors where the Prisoner nature of the game remains,
and Pareto-inferipr results are obtained. The point is that those rational, individual,
maximizing choices aggregated in the supergame can lead to Pareto-optimal results.
This provides a powerful criticism to the use of such welfare maximizing difficulties in
the tragedy of the commons and Prisoners Dilemma as a justification for the
I
necessity or imperative of the state. Even assuming a difficulty in maximizing social
welfare does not imply that the coercive state is the only or best solution. To say this,
however, is only a critisim of state justifications. These results of the supergame
analysis do not provide any positive rationale for the type of anarcho-syndicalist society
I have presented!
The moral claim of the anarcho-syndicalist vision lies in the freedom of perpetual
individual revolution, of individuals who have the ability to withdraw from any
association at a very low comparative opportunity cost relative to that cost when the
67


state claims soveriegnty. That revolutionary disassociation and voluntary association
could be incorporated into a system of social organization that approximates the
analogous free market situation in economics. It is the antithesis of Wells utopia where
[t]he welfare state governed by the samurai sees to it, as to a lesser extent do such
states as exist today, that every citizen is properly housed, well nourished, and in good
health, reasonably clean and clothed healthily (Wells, 1967, p. xvii). Wells totalizing
version of the welfare state into the World State sacrifices individual freedoms for
rational individual and social maximized happiness. But as Doestoevskis underground
man, a version of the radical individual anarchist, proclaims, a human is not a cipher.
Human society cannot be reduced to the slope of a tangent line on a curve of maximum
welfare. Society has borne the tragedy of that heart of darkness many times before. But
that tangent line can be used as a basis for individual decision-making. That allows an
expression of the contradiction of the rational nature of human beings who can fully
recognize the meaning of that tangent line and of two plus two equals four, yet choose
to put their tongue out at it. This the Prospects vision attempts to do and utopian
I
political theory allows us to contemplate.
Without a utopian commitment to question the underlying assumptions of
social practices, proposals for reform tend to bypass the central problems, and
may ameliorate a situation which ought never to be tolerated. Secondly, as
Kropotkin indicates.. .there is often historical evidence that what seems
utopian to one generation is accepted as obvious good sense by their
successors. Oscar Wilde commented that A map of the world that does not
include Utopia is not worth even glancing at, for it leaves out the one country at
which Humanity is always landing... (The Soul of Man under Socialism,
43). Thirdly, as Kropotkin also emphasized, most people are prisoners of their
own education, and of the reigning conventional wisdom. So their view shuts
out large stretches of historical experience, alien areas of social reality, and a
vision of future possibilities. (Carter, 1971, p. 83)
68


This chapter has presented the philosophical end behind the Prospects vision. It is a
model that faces both historical and logical limitations, but ones that are demonstrated to
be within the range of a functional system at some minimal level with information
technology as a means. The three braids of analysis of the Prospects vision, utopian
political theory, information technology, and anarcho-syndicalist theory are complete.
I
69


CHAPTER 6
CONCLUSION
What I have tried to accomplish is not a proof Thai information technologies,
computers, and their related intercommunication technologies, provide the technical
imperative to rationally choose a democratic form of feasible, functioning anarcho-
syndicalism. Rather I have attempted to demonstrate the prospects for such a system
being feasible and functioning.
I am no technocrat or technological pollyanna. While the central and critical
proposition of this thesis is that an anarcho-syndicalist type of political system not only
can be implemented using information technology as a tool to overcome limits of size
and information flow, but is preferable because it expands the personal power and
responsibility of the individual and the community in alienating cultures and economies,
I do not believe that the experience nor research of modem society is that technological
fixes, growth as the goal of an economy, nor unceasing technological innovation, will
solve the problems of the human condition.
I do believe that given the present set of circumstances of social life and
organization as the basis for speculation of alternatives, that technologies can be used as
integral tools to overcome certain physical and social limits that constrain the
possibilities of creating non-coercive and non-authoritarian systems along the lines of
anarcho-syndicalist theory. This leaves the question of the malleability of individuals
and their psychology and the perfectibility of social life completely out of the picture, or
at least at its very edges. Neither of these issues need enter into arguments concerning


the establishment or functioning of an alternative society whose ends are desirable and
whose means for achieving those ends are just, fair, and based on a radical equality.
Perhaps reduced population over time, a healed environment, small-scale social,
political, and economic organization, and a sustainable lifestyle would liberate human
beings in greater quality and depth than any form of mass, technological society, but
that is not the question, because that is not where many of the communities of the world
exist, nor where most are headed.
In that vein what I have discussed is not Utopia, nowhere, but rather Eutopia, a
good place, one where all the problems of humanity remain, but in a dynamic and fluid
flow of power, authority, and responsibility that does not tend to magnify foibles into
the forte of state, institutions, and rigid authority. It is a vision of a society where
specialized administrative and complex information is readily available, where an
approximated free market exists in real time and where price, supply, demand, and
other microeconomic effects respond to real information in real time, and where the cost
of information flow and decision-making are reduced enough to allow all who wish to
participate to do soall with the same technology. It is a vision where society and
civilization are an aggregation of the social and civil nature of individuals and the
communities they chose to form and maintain, rather than a set of institutions that
require the sacrifice and alienation of untold numbers of people.
71


I
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i
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1
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74


INDEX
Adams 27
Arrow 49, 50, 51, 52, 53, 55, 56
Bacon 37, 48
Bakunin 56
Becker 46
Bellamy 7
Beniger 3
Bookchin 63
Borda 50
Bronowski 1, 28
cable 42,43
Campbell 46
Carter 35,68
Catlin 32
CATV 43
Chadwick 46
Condorcet 50
decision-making 4, 5, 23, 31, 35,
40, 44, 58, 60, 62, 68,71
Doestoevski 68
Dolgoff 60
Engels 28, 61
Eutopia71
Freud 29
Galton 50
Goodman 47
Goodwin 6
Green movement 4
Hardin 65
Heinrich-Hertz-Institute 43
HHI43
Heisenburgs uncertainty principle 48
Hobbes 35, 55, 59
Horowitz 6, 7, 60, 61, 62
Hume 67
Institutional Possibilities Frontier 41
IPF41.48
Kaiser 43
Kelly 49, 50
Kropotkin 68
Laplace 50
Luce 65
Lynd 32
Mannheim 31,45
Marius 2
More 2,7
Utopia 2,27
Nabokov 1
Nanson 50
Nozick 33
Orwell 7,38
dystopian 33
Ovid 7
Pelloutier 61
Plato 7
Plattel 28
Production Possibilities Frontier 41
PPF41
Proudhon vii, 6, 33, 64
Qube 42
Raiffa65
Rawls 6, 52, 54
Rhodes 32
Utopia 32
Ricardo 55
Sarvodaya movement 4
Shelley 38
Sibley 37, 38
Skinner 31
Slaton 46
Smith 55
social choice theory 5,49
Sorel 56
Sugden 51, 52
Taylor 58, 59, 66, 67
Tehranian 4, 38, 42, 45,46, 47,48
Teich 3,47
tele-education 43
teleshopping 42
Televote 46,47
televoting 46,47
Trade unionism 6,60
Walters 30
Wells 68
Utopia 68
Westin 44
Wright 37
75


70
Appendix 2 A
CH3C- II 0 108 C>CH3 c7h80 oh
108[53,M+], 107[ 100, M+-H], 90[32, M+-H20], 77 [42,0- ]
107 108 109 110 111 112 113 114
100 77.3 0.43
OH B*1 h2o 5.60 100 87.7 10.4
0.128
A1 d2o 5.21 78.5 0.89 100 76.0 40.1 100 52.8 6D
0.047
C*5 d2o 5.02 3.2 25.4 77.5 100 84.1 42.0 12.7 100 30.0 6D
0.087


71
Appendix 2 A (continued)
CH3C- II 0 94 <0>_OH c6h6o

94 95 96 97 98 99
100 6.62 0.38
OH B*1 h2o ND
A*1 d2o ND
C*5 d2o 4.21 0.013 100 91.3 22.1 100 24.0 5D


72
Appendix 2 A (continued)
CH3C- II 0 136 hch£>ch3 CaHjo 0
136159, M+], 119[51, M+ OH], 91 [100, M+ C02H]
135 136 137 138 139 140 141
100 8.85 0.75
OH B1 h2o 6.3 100 10.6
A*1 d2o 84.0 100 87.3 4D
C5 d2o 29.5 71.4 100 81.8 50.2 18.1 100 35.7 5D


73
Appendix 2 A (continued)
CH3C- II 0 198 H -- CH2CH2 C14Hi40 H-0
198[23, M+], 107(100, M+ 0CH2]
198 199 200 201 202 203 204 205
100 15.4 1.30
OH B1 h2o 13.75 100 17.6
0.040
A*1 d2o 13.72 100 77.6 7D
0.054
C5 d2o 13.71 75.1 100 76.6 64.2 100 83.5 7D
0.022


74
Appendix 2 A (continued)
CH3C- II 0 226 H_(nH0>CH2CH2'O c15h14 2 other unidentified peaks

226 227 228 229
100 16.5 1.68
OH B1 h2o ND Y
A1 d2o ND Y
C*5 d2o 16.05 100 100 63.2 3D Y
0.021


75
A
P
P
e
n
d
i
x
2-B
nh2 92 <@>-Ch3 C7Hs 3D
H C*1 d2o 1.94 90 91 92 93 94 9 5 96
100 7.69 0.25
0.205 27.6 100 86.8 23.2 5.4 0.8 100 23.2 13.1
H 92 C7H8 <0>-CH3 3D
H C*2 d2o 1.94 90 91 92 93 94 9 5 96
100 7.69 0.25
0.264 22.7 90.7 100 42.5 10.4 1.4 100 23.0 3.3
CH30C n 0 92 C7H8 -ch3 3D
H C*3 d2o 1.94 90 91 92 93 94 9 5 96
100 7.69 0.25
0.180 5.9 33.7 100 94.2 38.6 10.2 1.8 100 26.0 4.6
ITI-CF3 92 <0>-CH3 C7H8 3D
H C*4 d2o 1.94 90 91 92 93 94 9 5 96
100 7.69 0.25
0.160 5.0 37.5 100 86.0 24.1 3.0 100 28.0 3.4


76
A
P
P
e
n
d
1
x
2-B
cont.
nh2 107 NH2 -<0> CH3 C7H80 5D
H C*1 d2o 5.34 107 108 109 110 111 112 113
100 7.73 0.46
0.121 3.4 15.4 61.8 100 61.8 30.7 7.7 100 49.6 12.0
H
H C*2 d2o


CH30C u 0 136 C0H0O2 H0Ch(o>-CH3 0 4D
H C*3 d2o 8.32 136 137 138 139 140
100 8.85 0.75
0.140 41.5 100 97.8 46.5 14.5 100 31.2
m-CF3 160 C0H7F3 ^0>-CH3 CF3 2D
H C*4 d2o 2.22 159 160 161 162 163
100 8.76 0.34
0.064 14.9 57.2 100 46.5 7.9 100 11.2


77
nh2 197 NH2 ->-CH2CH2 -(o) C14 H15 N 5D
H C*] d2o 14.48 197 198 199 200 201 202 203 204
100 15.8 1.16
1.440 6.3 11.4 64.3 100 91.7 45.8 12.4 2.9 100 27.0 6.3
H 182 Hh(o)-CH2CH2 - c14h14 30
H C*2 d2o 11.18 179 180 181 182 183 184 185 186
100 15.4 1.10
2.387 60.4 100 100 40.7 7.4 100 18.2
CH30C ii 0 240 CH30C -(O)- CH 2 CH 2 - 0 Ci6H1602 1D
H C*3 d2o 11.15 240 241 242 243
100 17.6 1.86
0.245 100 41.0 12.6 5.4 100 30.7 13.2
m-CFj 250 <^0^~ CH 2 CH 2 -(O) Cl5H13F3 CF3 2D
H C*4 d2o 11.06 248 249 250 251 252 253 254
100 16.4 1.26
1.832 100 66.2 44.4 11.1 1.8 100 25.0 4.1


78
A
P
P
e
n
d
1
x
2-B
cont.
nh2
H C*\ d2o


H
H C*2 d2o


CH30C u 0 182 c14h14 H_^0) dH2CH2 -(o) 4D
H C*3 d2o 1 1.15 180 161 182 183 164 185 186 187
100 15.4 1.10
0.245 8.5 5.6 13.2 85.0 100 50.5 19.0 5.5 100 37.6 10.1
m-CFj
H C*4 d2o




79
A
P
P
e
n
d
i
x
2-B
cont.
nh2
H C*1 d2o


H
H C*2 d2o


CH30C ii 0 226 H OC ~^0) CH 2 CH 2 ~^0) 0 C15H14O2 4D
H C*3 d2o 16.18 226 227 228 229 230 231
100 16.5 1.68
1.352 48.3 100 93.2 52.8 23.6 6.5 100 27.5
ITI-CF3
H C*4 d2o




80
A
P
P
e
n
d
i
x
2-B
cont.
nh2
H C*1 d2o


H 180 Ci4H12 ID
H C*2 d2o 13.14 176 177 178 179 180 181 182
100 15.3 1.09
0.086 11.8 7.8 49.7 100 100 49.9 11.8 100 23.6
CH30C ii 0
H C*Z d2o


m 248 / V. ^ H C*4 d2o 13.0 247 248 249 250
100 16.4 1.25
0.025 26.3 100 53.1 12.8 100 24.2


81
A
P
P
e
n
d
i
x
2-B
cont.
nh2
H C*1 d2o


H 178 C14H10 2D
H C*2 d2o 13.93 176 177 178 179 180
100 15.3 1.09
0.031 39.4 19.9 100 51.9 39.4 100 75.9
CH30C ii 0
H C*3 d2o


ITI-CF3
H C*4 d2o




82
A
P
P
e
n
d
i
x
2-B
cont.
NH'
H
C*1
D20
H
H
C*2
D20
CH30C
ii
0
H
C*3
D20
m-CFj
H
C*4
D20
197
/
C14H15N \
NH2 CH CH3 X
4D
14.75
0.033
195 196 197 198 199 200 201
100 15.8 1.16
7.6 23.2 46.8 100 81.8 34.3 14.0
100 41.9


83
A
P
P
e
n
d
1
x
2-B
cont.
NH2
H
C*1
D20
197
/
C14H15N \
CH3 N
^-CH2-<0>
NH2 /
3D
16.56
0.264
195 196 197 190 199 200 201 202
100 15.8 1.16
6.2 21.2 47.9 100 97.8 46.6 12.0 2.3
100 25.7 4.9
H
C*2
D20
CH30C
11
0
H
C*3
D20
ITI-CF3
H
C*4
D20


84
Appendix 2 C
CF3 160 ^0)ch3 CF3 C8H7F3 3D
160 [32, M+], 141 [10,M+- F] 91 [100,M+-CF3]
158 159 160 161 162 163
100 8.76 0.34
OH B*2 h2o 2.23 0.100 4.5 31.8 100 7.7
A*2 d2o 2.23 0.053 22.0 85.1 100 37.1 7.1 100 18.7
H 92 <@>-CH3 C7H0 3D
92 [51, M+ ], 91 [100, M+-H]
89 90 91 92 93 94 95 96
100 7.64 0.25
OH B*3 h2o 1.95 0.321 100 50.7 6.1 0.006 100 12.1 1.3
A*3 d2o 1.94 0.145 1.6 3.4 17.8 86.9 100 52.5 15.5 2.2 100 29.5 4.2


85
Appendix 2 C (continued)
cf3 174 ^>-ch2ch3 CF 3 CgHgF3
174[25,M+], 159 [100, M+ ~ CH3] 155 [ 11 ,M+- F] 105 [18, M+- CF3 ]
174 175 176
100 9.87 0.43
OH B*2 h2o 3.13 0.017 100
A*2 d2o ND
H 106 -ch2ch3 C0H1O 4D
106 [24, M+ ], 91 [100, M+- CH3 ]
105 106 107 108 109 110
100 8.80 0.34.
OH B*3 h2o 2.76 0.000 21.3 100 19.1
A*3 d2o 2.74 0.026 30.7 100 58.3 26.2 100 44.9


86
Appendix 2 C (continued)




OH B*2 h2o
A*2 d2o
H 94 /\ (g/- oh C6H60 4D
94 [100, M+ ] ,66 [50, Cp- ]
94 95 96 97 98 99
100 6.62 0.38
OH B*3 h2o 4.27 0.009 100 10.9
A*3 d2o 4.13 0.062 91.3 100 16.5


86
Appendix 2 C (continued)
cf3



OH B*2 h2o
A*2 d2o
H 94 /\ <0)-OH C6H60 4D
94 [100, M+ ] ,66 [50, Cp- ]
94 95 96 97 98 99
100 6.62 0.38
OH B*3 h2o 4.27 0.009 100 10.9
A*3 d2o 4.13 0.062 91.3 100 16.5


Full Text

PAGE 1

I I I THE }lROSPECTS OF INFORMATION TECHNOLOGY FOR A I FEASIDLE, FGNCTIONING ANARCHO-SYNJ?ICALIST DEMOCRACY by Curtis D. Holmes B.A., University of Denver, 1984 A thesis submitted to the Faculty of the Graduate School of the University of Colorado in partial fulfillment of the requirements for the degree of Master of Arts Department of Political Science 1991 :,{'S'"!l ... f\_:." i

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1bis thesis for the Master of Arts degree by Curtis D. Holmes has been approved for the Department of Political Science by ?adde Tecza Date

PAGE 3

Hohnes, Curtis D. (M.A., Political Science) The Prospects Information Technology for a Feasible, Functioning Anarcho Syndicalist Thesis directed by Professor MichaelS. Cummings Many anthropological and political researchers have demonstrated that societies approximating anarcho-syndicalist ideal of functional authority without coersion by the state, and of functional economic subgroups where members share radical equality, exist in small-scale, low-technological groups. The central focus of this thesis is the prospect of information technologies providing a means to organize a feasible, functioning society approximating the same anarcho-syndicalist ideal in mass, developed Caution must be exercised when speculating along these lines by applying social sCience methods to meet some minimum standard of logical coherence and consistency, and by identifying key concepts and lines of inquiry that are central to the constructs of a society. Visions of the "good" political society have I traditionally taken the form of utopian fictional literature. I use the precedent of that I tradition to construct a vision of that society, followed by an analysis of the vision as I related to its theoretical, technological, and anarcho-syndicalist characteristics and Throughout each element of analysis, utopian, technological, and I I demonstrate criteria that the political vision meets, and limits that it functions withi4. While too broad to consist of a proof that such a society is feasible and functional, I qonclude that the prospects indicated by analysis within these core areas are There is no implied moral imperative that such a society should arise, only that it possible and desirable under certain conditions and circumstances. The form and content_% abstract are a proved.! recommend its publication. Signed Michael Cummings Ul

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Dedicated to the of Vincent and Olive Holmes.

PAGE 5

CON1ENTS .................................................................... vi CHAPTER 1. INTRODUCTION .............................................................. 1 2. TilE "PROSPECTS" VISION ................................................ 9 3. Tiffi UTOPIAN ANALYSIS ................................................ 27 4. TilE 1ECHNOLOGICAL ANALYSIS .................................... .40 5. TilE ANARCHO-SYNDICALIST FOUNDATION ...................... 58 6. CONCLUSION ................................................................ 70 BIBLIOGRAPHY ..................................................................... 72 INDEX .................................................................................. 75 v

PAGE 6

I would like thank the Political Science Department of the University of Colorado at Denver and Of. Michael S. Cummings, Dr. Joel C. Edelstein, Dr. Glenn Morris, and Dr. Thad Tecza in particular for a challenging and inspirational learning experience and dialogue, and alsp for the opportunity to pursue speculative theory. I wish to thank I Kevin W. Perizzplo, Leslie Petrovski, Mary V.G. Lindesmith, and Roxanne Birlauf for their much assistance and patience. I give special thanks to Ron Strube, Esq., for more inspiration and insightfulness than can be expressed. Finally, I wish to thank all .the friends, family, and colleagues who have encouraged and supported the' dissident and somewhat cranky views of a professional malcontent Vl

PAGE 7

"Nihi,l motwn ex antiquo probabile est" : Distrust all innovations, wrote Titus Undoubtedly it would be better were man not compelled to change, qut what! Because he is born ignorant, because he exists only on condition of gradual self-instruction, must he abjure the light, abdicate his reason, and abandon himself to fortune? Perfect health is better than convalescence. Should the sick man therefore, refuse to be cured? "Reform, reform!'':cried ages since, John the Baptist and Jesus Christ "Reform, reform!" cried our 1father fifty years ago. And for a long time to come we shall shout, Reform, reform! Pierre Joseph Proudhon, Property and Revolution vii

PAGE 8

CHAPTER 1 INTRODUCTION Man the Uto.pia Maker The n,ame of the planet, presuming it has already received one, is immaterial. At its most favorable opposition, it may very well be separated from the earth by only as many miles as there are years between last Friday and the rise of Himalayas-a million times the reader's average age. In the telescopic field of one's fancy, through the prism of one's tears, any particularities it presents should be no more striking than those of existing planets. A rosy globe, marbled with dusky blotches, it is one of the countless objec'ts diligently revolving in the infinite and gratuitous awfulness of fluid space. 1958,p. 160) When I first read this initial paragraph of a short story by Vladimir Nabokov, it I struck me like the lost chord-the most perfectly rendered paragraph of English language that I had read. It has continuously transformed its meaning for me, and it strikes me now as a perfect description of the way that people project the world as it should be through their imagination. It is both universally general, a world that approximates our .own enough to be clearly recognizable, and detailed, radically differing to conlni;St the daily "is" with the "ought" Jacob Bronowski in his essay exploring the nature of cultural evolution, The Ascent of Man, discusses, the unique psychological trait of humans of foresight. S.o far, there is nothing to distinguish the athlete from the gazelle-all that, in one way or another, is the normal metabolism of an animal in flight But there is a cardinal difference: the runner was not in flight The shot that set him off was the starter's pistol, and what he was experiencing, deliberately, was not fear but .... In themselves, his actions make no practical sense at all; they are ari exercise that is not directed to the present The athlete's mind is fixed of him, building up his skill; and he vaults in imagination into the future. (1973, p. 36)

PAGE 9

From this ability to envision the future, people have contemplated and projected a meliorated politi,cal and economic society for all recorded history. In the Western scholarly tradition, Thomas More gave us the long-standing name, Utopia. "But in Utopia, as later on, we fmd the Thomas More who saw the world as a wicked place and the human heart as a pit of darkness requiring the light of diligent public scrutiny if the monsters lurking there were not to crawl out and devour the person and the society. More began Utopia in a church" (Marius, 1985, pp. 154-155). More's genesis of Utopia in a church is prophetic of a long history in Western utopian thought of antiestablishment establishmentarianism. The effon to reform the ills of the world often results in outrage at the state of current institutions because they are not ones that we envision-so the utopians propose new institutions to replace them. I call attention to this aspect of utopian literature, because I would like to distance the thesis from it The I thesis does not assume the necessity of absorbing the individual into some collective will or reformed conununal institution to retain utopian characteristics. It does not, as More does, criticize inunoral or inefficient social institutions by deifying others, but rather measures the power of utopian vision by comparing means and ends and their relationship to one another. The notion of the meliorative perfectibility of people and their society always begs the question of present circumstances--how did we get here and where to go from here. The utopian: nature of this thesis dwells on the political will of individuals in society to shape ends and means, not on the perfectibility of either. The Role of Information Politics is dependent on conununication, and conununication is limited by a number of factors and characteristics of reality as we know it. Geography and the limits of 2

PAGE 10

people to travel ;rre two of the most important; diversity of language and culture are others. The purpose here is not to identify and itemize a list of limiting factors, but rather to recognize that homo faber, man the maker, by the ability to conceive a technos has continuous!);' remade the nature and scope of those limiting factors. The products of the hand of people, technology, are intimately linked with communication and politics and in many cases provide the imaginative qualities and the limiting reality of utopian political visions. The relationship of technology to politics is often only explored on the way that innovation, assessment, control, production and so on are influenced by the political environment and how political organization (e.g., bureaucracy) can affect technological development. Yet the relationship extends far deeper and wider. It exists at the level of form and control itself. And, in tum, political form determines not simply the efficiency of production of this year's Christmas gift fad, but the existence and of how progress is defmed and the costs that society is willing to pay for the production of goods. In The Control Revolution, James Beniger describes in more detail the specific type of technology that I am interested in, information technology, and its relationship to social control. Because both the activities of information processing and communication are inseparable components of the control function, a society's ability to maintain control-at all levels from interpersonal to international relations-will be proportional to the development of its information technologies. (cited in Teich, 1990, p. 54) One of the ongoing and sharply divided battles in the discussion of issues concerning technology is its inherent nature: good, bad, neutral, all of these? Therefore, in this of computer and information technologies and how they 3

PAGE 11

interact with political structures, the perspective called techno-structuralist, elaborated by Tehranian will be used. (1990, pp. 212-217) In this viewpoint, technologies are neither good, bad, nor neutral in and of themselves. "This is because they developed out of institutional needs (in the case of infonnation technologies, primarily military and business needs) their impact is always mediated through the institutional arrangements social forces ... (Tehranian, p. 5). In other words, technologies always feed into social and institutional paradigm and have good, bad, and neutral effects. It is the way that the paradigm uses and understands the technologies that will I determine the greatest effect of that technology. Computers, especially when linked to other information technologies, have both centralizing--<:ontrol, privileged, barrier ridden and decentralizing-universal, autonomous, and democratic characteristics. Those characteristics develop in I accordance with the nature of the environment of computer use and the time and place of use. The prorriise of computer infonnation technology is the revitalization of a form of direct democracy and autonomous decision-making; the peril, a highly centralized, controlled totalitanan state (with a level of totalitarianism perhaps yet unseen). Prospects also exist for transformation of politics into new forms of association that are less possible or limited by the scale of societies in the absence of computerized information technologies. Tehranian discusses this aspect of computer politics in terms of a Communitaian Democracy. As extensions of our senses and as leverages of power, technologies replicate as well as augment the existing power relations. (Tehranian, 1990, pp. 201-212) In its ability to augment, Tehranian discusses the I Green movemen,t in West Germany and the Sarvodaya movement in Sri Lanka as case studies of communitarian value movements or parties whose potential for large-scale 4

PAGE 12

reproduction political power has grown and developed along with the information technologies. : I I An important political analysis that must be included in any exploration of current and future political implications of the computer, at the national level in particular, is social choice the.ory, presenting mathematical and logical limits to computational aggregation and :computer politics. "Technology can indeed make democracy possible in places where it was not I possible before. But the possibilities are not boundless. The bounds are set not by technology but by logic" (McLean, 1989, p. 2). Assessment of computer politics is based then on the limits to the very logic systems of which computers are built, but we must asswne new logic systems can and will be created that we cannot yet account for nor anticipate. The Anarcho-Syndicalist Moclel The thesis' fmal conceptual element is the foundation of the political theory vision of the social and economic system that I argue can be created given the political will to integrate information technologies into political decision-making and to dismantle current institutions. I have chosen as an historical basis the views of anarchosyndicalists with democratic variations. Anarchism speaks to the political questions of property, the state, and the relations between the individual and the state. There was perhaps never an anarchism, but many anarchisms, and they have contributed more in the areas of social critique and political philosophy than in any practical and long-lived organizations and associations. Yet practical political application of a philosophy is only one part of its value and not necessary for some form of validity. But for this thesis it is 5

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I a critical requirement that practical application and continued functioning be possibleI that is where I will flesh out the path I think possible. The syndicalist side speaks to the economic questions of ownership, material I wealth, need, supply, production, consumption and the link between the economic I enVironment and the structure of living. Trade unionism was the focus of syndicalist thought historicilly, but I have taken the philosophy to what I consider its logical conclusions, in worker-owned and democratically managed finns. Information technology is only an integral part of the operation of such firms but also implies a certain level of P,roduction, technological development, and growth that must be explored to a full picture that answers questions concerning sustainability. There are also two important questions about the parameters of democratically managed firms: (1) What areap:gropriate decisions that society as a whole needs to make-the macroeconomic .questions, and (2) What are appropriate decisions that organizations at the level of the need to make-the microeconomic questions William: Goddwin in Rights of Man and the Principles of Society practically ignores the question of economics and favors a rational analysis based on individual psychology.' This is how he builds his vision of anarchy and radical egalitarianism. He states, "Society is nothing more than an aggregation of individuals" (Horowitz, 1964, p. 113). Yet it is!that aggregate-for which we invented a word, society, that also must be accounted fot and its characteristics included in any feasible theory of anarchism. Pierre Joseph Proudhon analyzes from the perspective of Justice (later also reflected I in the work of Rawls) and states in Property and Revolution, These then are the three fundamental principles of modem society, establishbd one after the other by the movements of 1789 and 1830: 1) Sovert7ignty of the human will, in short, despotism. 2) Inequality of wealth and rank. 3) Property-above JUSTICE, always invoked as the guardian angel I 6

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I of sovereigns, nobles, and proprietors; JUSTICE, the general, primitive, of all society. (Horowitz, 1964, p. 106) In anarchism and syndicalism the question is always authority, but the analysis I revolves around ;the nature of the individual and the nature of the aggregate we call society. And, alt:>ng with Proudhon, that analysis must study sovereignty, equality (political and economic), and property. l These then are the three braids, utopian political analysis and theory, information technology, 'and :anarcho-syndicalist structure, that will be weaved together here to create a vision, and an analysis of that vision, for a new society. I intend to demonstrate I that such a society is feasible and functional and that information technologies make it possible to sustaJn that vision in a mass, developed, and industrialized society. While all three braids af'e vast areas, I have attempted to focus on the most important aspects I and criteria of ea;ch that applies to the main thesis. I From Ov1d (1st century BC to 1st century AD) through Plato, More, Bellamy, and Orwell, and fron:t utopia to dystopia, political writers have found that a literary expression of visions proves more effective and appropriate than political exposition or methodological social science. The literary style or fonn has a power to I conjure a world whole and communicate that world more directly than might be the case I with methodological exposition. This does not imply that there is a lack of method or valid analysis in expression, only that the style of choice differs substantially from scientific P\lpers. Following that tradition, I present a fictional account of the political and economic information society I see as an option. The method will follow. I The fiction a.t;1d the analysis explicitly treat the individual as primarily a rational actor and the view of tpat individual of the prospects for alternative systems as minimalist. If I the of infonnation technology along the lines explored would in and of itself at a level lead to greater freedom for the individual even without 7

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transforming the society and systems, then it is assumed a sufficient mtionale for following that While developmental ttansformation possibilities exist with information technology and are explored peripherally, those possibilities are not primarily important in the discussion of this thesis. 8

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CHAPTER 2 THE ,'PROSPECTS" VISION: A FICTIONAL JOURNEY The earth turning with its perpetually awakening inhabitants creates dawn as it has been doing and still continues to do; but the people, those groggy, flea-bitten, poor, rotten, conscious thinkers, ah, they had to discover that the sun never rises, that the sun does nothing but what the sun does and is no Apollo, but rather a big ball of gas. And Philemon, who prefers Phil, at present a lawyer on this little blue world, has a great deal to do. The trial committee had been formed several months ago by community decree and Phil, contrary to: usual practice, had volunteered to be case presenter. His skills were at least rusty after his years of teaching at the local learning center, yet he couldn't help but be intrigued by the "monster in their midst" as the press so jubilantly termed her. The questions to mind by this case were legion. They propagated, i overpopulated the legal mind and spilled, barren, into the quiet township street Daybreak is ;always the most productive thinking time for him, but today proved to be that irritating exception. He flicked the touchplate on the wall and waited for the room to luminesce. "My Mother," Phil thought, "always warned me about thinking and dressing at the same time. Focus, she always insisted, focus on what you need from the world or it will ignore you my little." He pulled on his typical jumpsuit, a thin grey coverall that had become the dress of the day. Dressing actually proved to be a simple affair I since people had let fashion and its constant change and frivolity pass into history. The one remnant of individuality was the personal vest that most people weaved, dyed or

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painted themselves, or with mother's help, and wore over the jwnpsuit He pulled it on, his thinking idistracted by the pattern. A full crest on the right side of the vest overpowered the remainder of the cloth. He had found this crest, a black and red circle with birds, long ago in a book he had been reading for entertainment. The pattern vibrated before his eyes and captured his imagination .then as it now captured his attention. He had decided then and there to add it to his vest as the powerful symbol of his future life. He didn't need to understand it; its meaning was forgotten anyway; it was the power he sensed in it that he wished to possess for his life. He flicked $e touchplate and left. First on the day's agenda was a visit to the learning center to arrange an indefmite absence. It was fairly routine, especially for case presentation, but, he suspected, the case and his role would become the talk of the community, which constantly led him to question his own motives in this affair. It had been, after all, several years since he last presented, and many would have wanted to argue this case. His almost ridiculous mythological stature in the community guaranteed his admission; however, when he chose to volunteer, he also made many mighty enemies at a stroke. Rounding the adobe-like passageway to the center he stopped shortly to adjust his attitude focus on the volley to come. Diana Strand, or S as she was known, would be the difficult and hurt victim in the drama around the comer. She was the center of a four-way marriage in the village and had been manipulating for what seemed decades to make Phil the fi,fth. She was sure to see his mad rush to volunteer for this case as a I desperate escape attempt from her, such was the narrowness of her thoughts. Quickly he tried to concoct some simple formula to try to open her awareness enough so that I she might see that this case was much more to him than everyday life and a simple 10

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appetite for adventure. But formulas wouldn't do. Her life was her marriage and the quadrangle that emerged from it. His concerns, thoughts, worries were beyond her scope; he had to leave her with that at least. "S, I need to talk with you-perhaps in private would be best." She remained quite calm yet verbally pounced his intrusion. "Can't you see, I'm teaching class?" S lowered her eyes and walked, shuffling, to the doorway. "I'm sorry; I didn't intend to be so terse, Phil. It's just that we needn't discuss it. I'll talk to you after the trial." The battle not fought, he reflected, can't be lost. *** Phil stepped.into an individual commuter car to drive to an interview and do some research about 60 miles from the village. The car operated on solar energy and had been built to last-12 years so far for this one. When he was younger and had little income I credit to use, Phil had entered into an agreement at one of the production factories that manufactured the cars. He worked in the factory for about four months producing the vehicles in order to drive off with one. Even though the cars were not privately owned, I they still represented quite a labor and material commitment in the community and required relatively high amounts of credits to operate. The benefit, however, of considering the complete transportation system as a public good-including vehicles had worked to the community's advantage. Rather than a consumable good, vehicles were now planned and produced as a capital good and engineered for extended lifetimes l to provide the mbst transportation and communication for the economic input. The factory experience had been the first time that he had become a member of a firm, even though this was by special temporary arrangement The engineers at this 11

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firm had devised the first operational production system for solar-powered vehicles that needed extraordiparily little battery storage. What storage capacity there was, usually was only neede4 for short periods of time in the worst of weather. Even most overcast days provided enough convertible energy to power the vehicle. His arrival at the plant was made official by a two-thirds vote of acceptance by all the worker-owners of the plant. Even though this kind of temporary work agreement had become fairly common practice, this factory continued to exercise full voting requirements for ratification of every new worker-owner. The vote was taken within the first fifteen minutes of the day when all the policy and day-to-day administrative business was performed at computerized information workstations available throughout the plant This real-time, on-line system allowed all1,200 employees to communicate, argue, and debate during the time limitations, and then to vote. The vote was tallied I almost instantaneously and the next agenda issue, agreed on the day before, became the issue at hand. At the end of all the voting, a summary of all decisions and administrative functions was provided to each person. Although some factories had randomized worker-owner roles. within the plant, called facetiously by some, role de jour, this factory had decided on more traditional elections for positions based on merit and testing. Those qualified could run for the various administrative positions of trust and authority. The number of terms, however, were strictly limited to one, and all office holders returned to other positions. The only exception was the engineering departtnent where the head engineer could only be removed by a vote of no confidence. Such was the power of specialized knowledge. I The head engineer in this plant, however, received far lower income credits because of his powerful position. 12

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Phil had extremely happy that this plant was not based on randomized roles as he wouldn't to be distracted by potentially being a candidate during every vote. As a temporary employee, he preferred to work on the car to earn factory credits, rather than in some administrative or specialized position. He did fill in for a sick worker-owner for several days in the materials ordering department just before leaving. He left with a mountainous headache daily as his distaste for mathematics fought with his understanding. The ordering computer was interlinked to many of the main materials suppliers of the factory and also to the central ordering computer that any producer could link with. The computer kept constant track of inventory and daily use, attempting to minimize warehousing. Phil's job those few days was to fmd needed materials on the computer market, order, and arrange for transportation. All the income credits and costs in terms of time and value were calculated based on the agricultural supply. Phil mused while ordering a quantity of metal from a factory up-river about his inability to understand how people had seriously placed value, real value, in gold and other metals as carriers of economic worth. That could only happen in an economy abundant with agricultural goods or in such authoritative control that those without fOOd had no avenue of action available. The agricultt,rral supply had been good this year, and the calorie allowance had been going up for several years-some claimed to ridiculous heights. At the time, calories had become quite the controversy. Agricultural goods and value-added foods were also available to all on the computer market, but you could only order a maximum calorie equivalent of fo6d That limit had now become so high, that many people ordered the most incredible amounts of chocolate cake and fat-added foods that many were calling for factories to limit production of such goods. 13

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The engineers at this and other vehicle production factories had taken the idea of the I vehicle as a capital social good so seriously and designed these solar commuters so well that orders for the cars had considerably slowed within the last few years-thus the new temporary agreements arranged to moderate the necessity of decreasing work before people chose to leave. It was, however, work that was reduced and not the worker-owners numbers as the bull or the bear within the plant was borne equally by all. The plant hatl no legal status, such as a corporation, but rather operated under the current rules an4 policies decided by the community as a whole. Often this made some operations of the plant more difficult, but preempted the long-term abuse of loopholes in legal semantics by a corrupt few. In fact, many of the factories and work cooperatives changed status and structure often, sometimes evolving into groups that bore little resemblance to their original function or purpose. Long-term stability and purpose provided both a poor means for responding to change and a good environment for developing institutionalized and abusive authority over others. The difficulties inherent in constant change were understood to be a large part of the payment toward a freer life. I His first dayi of work, Phil participated as a full worker-owner in setting the agenda and making the decisions of the plants operations. His workstation began with the agenda from the, previous day-an election for a position that had opened after a retirement, a on the reduction of the work day to 5.5 hours caused by dropping demand, a rise automobile pricing to compensate for lost income from the long-term drop in demand,: an arbitration vote on the complaints of the factory manager with the current chief of material acquisition, and a setting of the next day's agenda. 14

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As a student of law at the local learning center, he was very interested in the arbitration vote and how the factory handled such disputes. Apparently, all complaints I had to be made publicly before any remediation is possible. The factory manager had accused the chier of under-ordering certain materials in the solar electronics deparnnent to make the department's production figures look bad. Apparently, this was a personal vendetta. The charge had been made public at the plant several weeks before and a simple majority of worker-owners had voted the charges severe enough to warrant investigation and arbitration. A committee of three randomly chosen worker-owners was established to conduct interviews and to review any appropriate documents. They were given three weeks to report. Both reports had been available on the main computer now for one week, and the I arbitration committee's report and recommendation was to be voted on. Phil took this I act very seriously and reviewed the committee's recommendation, the statements of both parties, anq a dissenting view provided by an interested worker-owner. It seemed to be fairly clear that the chief had been under-ordering certain materials that were readily available on the computer market, but was less obvious as to why. The under-ordering was enough of a concern to others in the plant that the vote clearly favored the report of the committee that irregularities did exist The appropriate response seemed to be removal of the chief, but other options were presented as well, including community service and liquidation of his interest in the plant Moderation won the day and he was simply removed from the role of chief of materials acquisition. Another position at the plant was randomly chosen for him. *** 15

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Phil's wandering thoughts on that first arbitration case at the plant brought his mind screaming back the task before him. His research would take him to a small agricultural and production cooperative about 60 miles outside of town. He was approaching the cooperative and flipped on the map chart just to make sure he had the correct one. He checked the map display cursorily as it was obvious that the building on the right, a farynhouse surrounded by donnitory-style housing, was the cooperative he was after. He pulled in and sat for a few minutes, building some strength and rehearsing his questions. Severn, the woman who was currently chief negotiator of the cooperative, appeared at the main farmhouse door and waved him in. He had discussed his reasons for coming several weeks ago on the phone but was unprepared for the brute strength and presence she seemed to possess. They greeted traditionally, shaking hands. "Levy is in the main dining room waiting for you," she opened the conversation. "The cooperativ discussed the problem at our last meeting and decided that he should be relieved of duties until the case is completed. He has chosen to stay with us even under these conditions. Be thorough, but don't drag this out" "I appreciate your directness," Phil blurted in return, "my intentions exactly." Phil entered 'the dining room. Levy was very stoic, and volunteered no information, I the perfect reactive personality. "When did you first meet her?" Levy seemed to slightly cross his eyes as he answered, "I don't see that my life is any of your concern." I "You will be asked many questions at the trial," Phil added, "you may as well get some practice in now." 16

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Levy evaluated his position and turned to the window answering every question directly but without embellishment Yes, he had met and admired her. Yes, he knew of her views, probably after the second meeting. Yes, they had met several times at night at the cooperative. No, he was not a member of her group. No, he would not name names. Enough practice. I Phil needed to access some public documents to substantiate members of the cooperative and 'attempt to link others to her meetings in the dark. He asked to use the fannhouse workstation and retrieved names of those he considered interviewing next Severn had made it clear, however, that for now his presence had been tolerated long enough. "Work to do," she stated and opened that front door once again for Phil. On his return trip Phil turned on the car radio and listened as each low-power transmitter, from cooperatives, some from small villages and towns, some just individuals ranting, faded in and out on the main channels. Many were discussing the upcoming trial, but luckily no one had used his name yet. Fame was rare in an age where everyone's 15 minutes of exposure to fame could stretch on indefinitely thanks to full public media access. One cooperative, as it faded in, appeared to side with many extremists, who, while not yet verbalizing it openly, were discussing the old uses of the death penalty. If you couldn't pick up their not-so-subtle implication that it was time to rethink the practice of forbidding death penalties, then you wouldn't realize the I serious implications of this case. As the faded out, the ashram Rama speeded into view and and retreated in the mirror with the temple sign of an avatar-like character holding a handful of onions and smiling somewhat awkwardly With over one million pounds of onions produced last year, the had a lot to smile about 17

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Phil went cfuectly home on his return to the city. He needed time to compile the information he had been researching into something that resembled a presentable case. The case was oqty three weeks away, and the jury had already been selected by computer rote. He flicked the touchplate, and the small cottage began to luminesce from the chemically stored energy from the day's sunlight The cottage was a small, well suited space for one person, and one of about fourteen cottages inhabited by those who taught and worked at the learning center. The cottages were in a wooded area about a mile from the learning center, far enough that Phil didn't feel a8 though he lived in his classroom or at the center, yet close enough to walk or cycle. Originally the learning center cooperative staff had worked and lived in a large mansion-sized home they had built themselves, but they found the close proximity of living and working led to frustration and anxiety. Some separation was required. It was then that the community as a whole, including volunteer students, built the cottages as a I living settlement away from the center. It had proven much more effective, though sometimes Phil thought even more distance would be an improvement He scattered his research, interview tapes, press clippings, and assorted artifacts on the floor. *** Her name was Sharon, and it seemed she had always been somewhat precocious. I Her childhood, 'or what was known of it, didn't provide any stunning psychological insights into her later activities, just a story of a very bright young woman with ambition. Her learning-center activities were average, although the learning center she had chosen to attend, while rigorous academically, had fought several accusations of supporting violent student organizations that had disrupted local town meetings and I work comriluniHes. It had been asked to disband once, but refused, then reformed into 18

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an exclusive organization that accepted no requests for admission. The admissions were by invitation alone. There were no indications that she had ever faced community sanctions, community exile, or a called trial. Apparently while she was carrying on the gravest of her activities, she had also contributed substantially to the communities of which she had become a member and was one of the highest producers on the cooperative where Phil had been conduc;ting interviews. On the surface quite a model. But below that surface .. *** The knock at the door brought Phil screaming back to consciousness. The room spun and shattered into a thousand spinning fragments. The spinning slowed and began to crystallize into a recognizable whole, fragment connecting to fragment until Phil's conscious mind looked out on a unified world that seemed to make some sense. Knock. The door. He stumbled to the door and foundS there, waiting impatiently. "Catching up on a little lost sleep?" she grilled. "Going to invite me in?" Phil only then realized that it was late evening, and he had fallen face-down asleep into the piles of papers detailing the case. "Oh, come on in," he said, "and I'll put on some tea." He assumed that this was to be another assault on his timing for taking this case and another blunt attempt to recruit him into her communal marriage, but his next thought I reminded him iliat she had given up cottage visits for this putpose long ago. "I've come to tell you," she drawled, "that I have been chosen by vote to be the I second case presenter and that we won't be able to have any contact after today." What a relief, thought Phil. "What an honor," he said. "Isn't the community a little behind schedule on appointments?" 19

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"Yes," said S, "but everyone feels that we must be careful on a case of this magnitude. It shouldn't be rushed in any way. We won't be able to speak for quite some time you "Uh-huh," said Phil, "but it will be much easier since we won't be at the learning center until the case is think we'll manage." After she Phil looked at the cottage walls and the papers on the floor. ''Perhaps the world doesn't make whole sense yet," he thought; "need more sleep." *** What makes this inquest significant is that these prisoners represent sinister influences that will lurk in the world long after their bodies have returned to dust They are living symbols of racial hatreds, of terrorism and violence, and of the arrogance and cruelty of power. They are symbols of fierce nationalisms and of militarism, of intrigue and war-making which have embroiled Europe generatien after generation, crushing its manhood, destroying its homes, and impoverishing its life. They have identified themselves with ... (Jackson, 1947, p. 31) I Phil stood before the court committee, the reporter overseeing the accuracy of the voice computer''s documentation of the case. Phil knew almost every workstation and home would be requesting full transcripts of the case each day. He began by quoting the paragraph from the first international war crimes trial in post-WWll Germany as a precedent, even during the time of state domination of politics, addressing the problem they were all about to confront in person. He spoke to the jury, the defendant, and the judge in this case, Jane. She was a member of an agricultural and small motor manufacturing community about 100 miles south: of the city. She apparently had a reputation for having a strong intuitive sense of justice and fairness and had been elected almost uncontested through three I court committees to act as judge in this trial. Her affect was stoic, and it was difficult to detect even the slightest of expressions on her face. Phil had learned long ago when 20

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practicing, however, that the limited role of the judge in modem cases didn't justify the time expense of"guessing the judge." He began carefully presenting all the facts of the case as he had found them. He explained the facts of her childhood, attendance at the academy and the accusations against it, her family background, associations, aspirations. And then, he delved into the crux of the case. Apparently while working on the agricultural cooperative, Sharon had begun forming discussion groups on political and business issues of the cooperatives. Were they producing too much? Was the role of subsistence farming for vegetables at the cooperative useful or a hindrance? But vegetable and aquaculture questions soon turned to authority and culture questions and the group began to lose members because of her tirades against radical equality, but gained others who had heard of her fiery speeches. Phil's interviews at the cooperative had demonstrated consistent stories of her flushed face and rising voice tearing at the fabric of social life at the community and causing serious dissentidns among newly formed groups there. Soon an elite group of her most ardent admirers formed, and when it was discovered they had been hoarding a significant amount of their production, they were asked to leave the community. But this was just the beginning. She wanted to form a core of radical loyalists that she could train to carry out her final solution; she wanted to build an armed group of shock troops who would begin to expropriate land and people for their new society. Those that wouldn't follow, wouldn't live. The anns stash that had been found buried at a small privately leased fann about 20 miles from the cooperative had been designed and built by her and the man everyone considered "second" in their secret society. They had used expropriated equipment and material from manufacturing section of another local commune that produced small 21

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I farm implements and machinery. They had developed molds and had manufactured a variety of short-range and long-range weaponry to meet the needs of her developing master plan to cqnquer and rule. They had also produced a great deal of ammunition and explosive de;vices through several worker-owners at a materials factory 200 miles I south of the city.' "This, above all," stated Phil, "demonstrates the extent of her malevolent irifiltration of our lives and our communities." I Witnesses then were called and facts substantiated. Faces turned in horror and awe as the extent of the threat she had posed and the close proximity of her soon-to-belaunched authoritarian war became clearer-the "monster in our midst." The judge p<)inted at Phil. "Have you completed presentation?" "Yes," he as she then pointed in the of S. "Second cas presenter." Phil listened as S presented a scenario vastly different from his own. This was relatively especially in cases this well researched, as neither presenter acts as advocate for but rather for the truth and the case committee. Most cases would show one presemer pointing out differences in fact that needed to be resolved or presenting different or more infonnation and interviews that tended to substantiate the validity' or invalidity of the charges against an individual or group. Phil couldn't help but wonder if S wasn't taking this opportunity to humiliate him personally for his marriage reluctarice. S portrayed an ambitious and acrid personality in Sharon, but one that did not deviate at all from the norms of an egalitarian and open society. The small arms, while of enormous concern, could not be directly linked to her except for testimony from witnesses who may be guilty of the offense and attempting to escape I justice. As for her advocacy of a more authoritarian system, belief in such a system had 22

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I long ago ceased to be classified as an offense, and she had been free to create such a I system within the structures of this society as long as participation was strictly voluntary, as PhU's presentation had clearly demonstrated was the case. I S also continued, demonstrating that in fact there was no provable conspiracy, that witnesses to profess that "the monster'' had indeed continued to participate in l both the decision-making functions of the f:ums and cooperatives of which she had been a member apd the daily social policy-making functions. How could such a supposed whose beliefs were the antithesis of the egalitarian ideal continue to I participate in a system? And finally, there had been no acts or deeds committed by Sharon or any of her followers that could be considered offenses. Phil thought about S' presentation and realized that even a callous belief that she was acting out of personal revenge discard the points she had raised. He thought she had thrown quite the :into the portrait the press had pieced together of this affair, but little did he know the ;whole case was about to blow wide open. After both ptesentations, the judge pointed to Sharon and asked if she would like to present her and facts of the to the jury. Indeed, she did. She began by I practically admitting all the established facts of the case, but then, in the described fashion, her beet red and the tirade began. "I challenge lfte very validity of this court, this case, these presenters, and any verdict of a straw-picked jury," she railed "By your own beliefs how can you enforce I i such a a verdict. How can you justify the coercive intrusion into my life and welfare, and how will you enforce it except by physical force? Because, opposed to the second presenter, I did construct and bury those weapons; I did form groups who plotted murqer m;td property seizure, and I will continue to build and plot until my last breath. This is no society. For you will have to destroy your society to enslave 23

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me and control actions and words. You will have to coerce and imprison and thus end your ideal, dr I will destroy it for you in a true society of nile by those who merit it; and it will have more wealth than your worker-owners, as jittery and gutless as birds who scatter at step, can ever imagine. you will end non-authoritarianism and the lack of a me, or I will do it for you. "We find your soft Utopias as white I As new-cut bread, and dull as life in cells,/ 0 scribes who dare forget how wild we are,/ How human breasts adore alarum bells. I you house us in a hive of prigs and saints I ., Communal, frugal, clean and chaste by law./ I'd rather brood in bloody Elsinore I Or I be Lear's fool, amid the straw./ Promise us all our share in Agincourt I Say that our clerks shall venture scorns and death,/ That future ant-hills will not be too I good I For Heru)r Fifth, or Hotspur, or Macbeth./ Promise that through tomorrow's spirit -war I man's deathless soul will hack and hew its way,/ Each flaunting Caesar climbing to fate I Scorning the utmost steps of yesterday./ Never a shallow jester any more! I Let not Jack Falstaff spill the ale in vain./ Let Touchstone set the fashions for the wise I Ariel wreak his fancies through the rain." (cited in Walters, 1989, p. vii) With Utat,1 a raised fist, and chaos in the court, the day ended. I Phil dichi't bieve that one person who was in that court today, or anyone who read : i the transcripts at :their workstation wasn't mulling about their whole society tonight as he was. He cou14 barely believe the power that Sharon had wielded in that room and the danger that she represented. This was as close to a coup, he supposed, as any society with no state apparatus could come. She had admitted her guilt and challenged the court to find :tier guilty and then control her without destroying its own ideals. Yet it had to be I The court again three days later as the jury had reached a verdict In his meditative state about society, Phil wondered at the continuation of the belief that those 24

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charged with offenses were entitled to face their accusers and the jury in person. It would have beeq. just as easy, if not easier, for the verdict to be polled at workstations and the sentence:carried out by a rote committee with the judge's instructions. But here they were in person, with a hundred-thousand people watching computer screens. The jury read the guilty verdict and the judge began the sentencing act with an explanation. "The defendant is found guilty of violating some of the most precious norms of our society. Contrary to her apparent belief, this is not a non-authoritarian society, but rather one in which authority is decentralized to individuals and to the aggregates that they voluntarily create. Those are the only legitimate modes of authority. But confusing this decentralization with a lack of authority to meet challenges to the continued and freedom of individual choice that you represent is to mistake weakness for strength. Contrary to your argument that we must destroy our most cherished beliefs to physically control you, we protect them. For we have not institutionalized our power and authority as you have done, and have not claimed any elite right to as you have done, but act individually and as a voluntary community to defend ourselves against those who would institutionalize their power and set us on the road to greater inequality and less participation. We make mistakes, but do not then defend our mistakes as a necessary and inescapable part of an institution, but constantly tend toward correction. You have demonstrated that for your own power, and those who follow you, you are willing to kill, injure, destroy, steal, and coerce. You are hereby, banished to the internal urban cooperative where you and others who have been previously banished are free to create your own society as you see fit However, all materials are limited, you cannot leave the cooperative for life, you will be provided with raw agricultural goods and implements only. This is the limit to our authority, an eternal vigilance against you and those who wish to enslave all but a 25

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minority of us as has been done in the past We exercise valid authority to protect ourselves to maintain our society, not to destroy it, by preventing you from destroying it in the name of some selfish glory at the expense of others. 'Do no harm,' is not just a physicians' pledge, but our own. And, 'do not allow harm' is its corollary." *** Phil returned to the cottage and flicked the touchplate as he entered the room. The sun was slipping under the horizon, that big ball of gas that had recharged the chemical walls that now luminesced. He sat at the workstation to order new coveralls and two new pairs of shoes (or his return to the learning center tomorrow. The request almost instantly entered the computer market that presented consumer demand and matched it to current and projected firm supply. A shoe factory 40 miles outside of the city matched the order and entered it into the production planning schedule for the next day. I They also autorriatically ordered enough material from raw producers to meet tomorrow's production demand, which was then picked up by a transportation cooperative and charged back to the material supplier. At ahnost the same moment, a second order for shoes arrived on the demand market from the internal urban cooperative. same process quickly fell into place with a second transportation firm picking up the order for 10 percent less charge than the previous transportation cooperative. The earth tupting with its perpetually drowsy inhabitants creates sunset as it has been doing and still continues to do; but the people, those groggy, flea-bitten, poor, rotten, conscious thinkers, ah, they had to discover that the sun never sets, that the sun does nothing but what the sun does and is no Apollo but rather a big ball of gas. 26

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CHAPTER 3 THE UTOPIAN ANALYSIS Is Uto_pia Serious? Chapter 3 presents an exploration of utopia as political theory and its value in social science as a process of model building. It also explicitly analyses the previous fictional section according to certain minimal standards of logic, for example, the requirement of linking means and ends coherently. Before exploring in some detail the social scientific process of elaborating the criteria of utopian political theory qua theory, I will discuss the nature and vaiidity of utopian literature and its place in a particularly political context using More and his Utopia as a primary example. There have been two schools of thought about More's Utopia from his contemporaries to the present day that are generally instructive (Adams, 1975). One school argues that the essential nature of Utopia is that of a joke, at best a satire intended to demonstrate the absurdity of English customs of the period by a "Most Distinguished and Eloquent Author." The other school argues that it is indeed a serious attempt by a man bent on creating a moral political order who presented the essential elements of "The Best State of a Commonwealth" with calculated hwnor. It is difficult, joke or ideal, not to take Utopia seriously at some level from a man who died at the hand of his king ,challenging the morality of political life, if not the whole social order. The good saint demonstrated that lethal seriousness in his advocacy of the burning of heretics as the church attempted to maintain a moral order. Those tWo sqhools extend in scope beyond the controversy of Utopia to all utopias. Is utopia a valid and important construct of our thinking and aspiration, or a bane to

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clear thinking and planning that leaves only utopia-as-joke with any validity? And as a sidebar, there is t,he whole realm of dystopia to consider, of utopia as the epitome of the bad joke. Utopian literature intends to transcend reality; dystopian literature to gaze into the crystal psyche of "manunkind"1 to delimit the fallout from the attempt Generally speaking, three variations can be distinguished in the definitions of the utopia The fJrSt conceives the utopia as a particular literary style and seeks the distinguishing characteristic of it in certain literary qualities. The second the utopia a "utopian," i.e., naive and prescientific, way of thinking about society, for example, in The Development of Socialism from Utopia to Science Engels seeks to distinguish an outdated and prescientific style of Saint-Simon, Owen and others from the scientific socialism based in the discovered laws of historic material development The third identifies utopia with the critical approach to the form man has given to society. (Platte!, 1972, pp. 41-43) Bronowski in The Ascent of Man, expresses one of the distinguishing qualities of human psychology, and perhaps the sine qua non, as the act of the vaulting athlete whose behavior is driven not by the immediate environment, but by a set of goal directed assumptions lying not in the present but in the future (1973, p. 36). It is a small leap to go this distinguishing quality of human psychology and imagination to the expression of those qualities through oral and written utopian constructs. From this perspective it would be the expectation of a constant and unavoidable expression of l"pity this busy monster,manunkind,/ not. Progress is a comfortable disease: I your victim( death and life safely beyond) I plays with the bigness of his littleness/electrons deify razorblade I into a mountainrange;lenses extend I unwish through curving til unwish I returns on its unself I A world made I is not a world of born-pity poor flesh I and trees,poor stars and stones, but never this I fine specimen of hypermagical/ ultraomnipotence. We doctors know I a hopeless case if-listen:there's a hell/ of a good: universe next door,let's go" "pity this busy monster,manunkind," is reprinted from COMPLETE POEMS, 1913-1962, byE:. E. Cummings, by permission ofLiveright Publishing Corporation. Copyright 1923,1925,1931,1935,1938,1939,1940,1944,1945,1946,1947, 1948, 1949, 1950, 1951, 1952, 1953, 1954, 1955, 1956, 1957, 1958, 1959, 1960, 1961, 1962 by the Trustees for the E. E. Cummings Trust. Copyright 1961, 1963, 1968 by Marion Morehouse Cummings. 28

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utopian thinking as an integral part of humanity, rather than utopia as a particular event or story by someone with an agenda. "The critical intention to break through the existing conditions and achieve a better future tum out to be the essence of the utopian phenomenon" (Platte!, 1972, p. 44). The critical view of utopia, however, presents it as a symptom of a simmering crisis, an expression of dissatisfaction with present circumstances and an imaginary vision of different, more amiable ones. And the dystopians warn of the consequences of such imaginative attempts toward change. Others declare that civilization is not an aggregation of the civil individual but the repressive means for survival of death seeking beings. ":According to Freud, civilization is essentially restrictive and repressive. With his pleasure principle man remains fundamentally an enemy of I civilization and its principle of reality" (Platte!, 1972, p. 1 09). The resolution of that contradiction lies in the old trick of moving to a more inclusive category where the contradiction disappears, or at least appears in a greater context Utopia as a critique and of does not exclude it as a normal and constant expression of human psychology toward the future; it is a subset of it And the failure of the scientific-socialist explanation of future reality lies not only in its many failures as a I predictive but also in its a priori assumptions and circular arguments where any historical event c3n fit into the theory to prove it but not to disprove it. or Transformation? So we are left with utopia; utopia that this thesis accepts as serious .. But is it a utopia that vaults:the present into future-oriented, non-existent circumstances, or a utopia that is a not-so-subtle justification for present circumstances, unable to break free of its material and social context? Karl Mannheim (1956) in Ideology and Utopia 29

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analyzes the disqnction between ideology and utopia. This distinction is used I analytically by Kerry Walters (1989) in The Sane Society Ideal in Modern Utopianism. I I Basically, WaltefS argues that opposed to a utopia that breaks the barriers of status-quo I thinking as a prefequisite to social change, ideology, often disguised as utopia, presents a picture of a status quo in a propagandist fashion that justifies the state of current I ideas, classes, artd institutions. Mannheim states, I every period in history has contained ideas transcending the existing order, but these!did not function as [nonideological ideas]; they were rather the I ideologies of this stage of existence.as long as they were "organic4!ly" and harmoniously integrated into the worldview characteristic of the period (i.e., did not offer revolutionary possibilities. As long [for instance] as the and feudally organized medieval order was able to locate its paradise butside of society, in some other-worldly sphere which transcended I history and dulled its revolutionary edge, the idea of paradise was still an I integral part of [the classbound ideology of] medieval society. (1956, p. 193) I "Utopias on other hand, are deliberate attempts to 'transcend' both 'objective' I reality and currently existing ideological structures" (Walters, 1989, p. 67). We have seen, following Mannheim, that utopian thought forms can be from ideological ones on the basis of the difference in their social Ideologies tend to support the conventional, normative and conceptual models operative in a given socio-economic context. As such, they I tend towards totalization, which in turn social and conceptual innovatiohs and leads to a stagnation which eventually gives rise to alternative utopian Utopias sense the tension between the putatively absolute standards: of ideological structures and actually existent socio-material I and strive to alleviate it by introducing alternative worldviews and social In doing so, they chip away at the ideological continuum, thereby as vehicles for social and theoretical innovation. (Walters; 1989, p. 72) I Here we can Walters' thesis that the "sane society ideal" in modem utopian i novels such as /..itoking Backward are ideology, ignoring class realities and, accepting Mannheim's (1956) distinction between ideology and utopia, ask if the previous 30

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chapter's Prospects vision is revolutionary or a redux of technology-based industrial capitalism. The first criticism that could be posed is that the vision of the prospects of info:rmation technology does not change in any fundamental way the nature of mass industrial production and consumption, but only rigidifies it by establishing a paiadox where human liberation, freedoms, and equality totally become dependent on a system of industrial, high-technology production and innovation, requiring the resultant industrial structure of living/working and work discipline that is by its very nature antithetical to freedom of choice. It could also be argued that such a high-technology dependent political and economic system will either create a new or sustain an old technocratic elite who will be able to wield an institutionalized form of i authority based on critical, specialized knowledge. This vision is little different than Skinner's (1948)Walden Two where a technocratic meritocracy will rise to power. The difficulty with Walden Two, and many utopian visions is their static quality. It is just that qualicy that is challenged the most by the Prospects vision. This is a dynamic society where no institutionalization of power nor crystallization of roles is legitimate. The latowledge of information technology auhe crux of the social, political, and economic decision-making is not of a nature that can be buried in a backyard vault, ' nor a single Yet the dissemination of such knowledge has to be planned, and the nature of temporary and rotating responsibility would make elite-formation because of this specialized knowledge very difficult In view (1956) distinctions, it is also evident that the Prospects vision is not a totalizing vision, but rather one that fragments political and economic society into voluntary aggregates who choose their own operating procedures through democratic means. As for it presenting a basis for a strengthening of bourgeoisie democratic-industrial forms, it is also evident that the basis of bourgeoisie class 31

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exploitation; ownership and property, are devolved to a system of worker' ownership, lease:s, and public/participatory disposition of wealth ari.d power that would I preclude class fopnation and would leave it to critics to explain the functional or material basis of such a class. Means and Ends The Prospeds vision once distinguished as a utopian, not ideological, expression of I I nonnative psychology (answering the question, "what if') can then be subjected to a set I of criteria of utopia as political theory. Harold Rhodes in Utopia in American Political I Thought discusses the "crisis" in American social science at the end of the 1960s and I links it to the crisis of modern utopian dramas. In effect, Rhodes calls for a critical I linking of means and ends in political utopia and one that meets the standards of Robert I Lynd and George Catlin that "Thus if the political scientist is to meet his responsibilities I according to the l--ynd-Catlin criterion, he must (1) perceive a problematic condition, (2) identify an alternative, and (3) specify a method for effecting that alternative" (Rhodes, I 1967, pp. 10-11); Rhodes, in attacking the "paradigmatic" view of political thinking outside of scient$c criteria, argues that the responsible social scientist can produce theory that links appropriate means and ends according to methodological criteria. Rhodes argues, and I accept the argument, that "ought" questions can be subjected to I investigation and: empirical verification and that the alternative of an inability of social science is the metaphysical slippery-slope of "ought" questions subject I only to human reason. Or, I would add, in light ofMannheim's criteria, "ought" questions then ideology. Problematic ondition. There are two problematic conditions that can be identified I in the Prospects The first is the political tension between democratic 32

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I participation the growing distance between state-enforced public policy and the i mass While arguments and research continue on the explanation for low voter participation in elections, the basic fact of decreasing participation in the political remains; this at a time when the information available to decisionI makers and to the public as a whole has increased exponentially. And when the speed with which the aggregation of voting has also increased significantly. This condition of the body politic remains a question of whose interests the state serves. In any system dedicated to the proposition that "all men are created equal, can the state remain I a neutral embodiment of that principle, or will it always drift toward serving the interests of one class above others? In his dystopian expose of revolutionary I development, Anj.mal Farm, Orwell proposes that any revolution that establishes an I authority wieldec;l by a minority will grow toward serving the interests of that minority at the expense an increasingly alienated population. If we accept the proposition that the ideal situation is one in which not only "do no harm, but also "do not allow hann, is operative, have we then backed into a minimal state that is justifiable as long as it protects the rights of individuals? Or as Proudhon states,: I To be GOVERNED is to be watched, inspected, spied upon, directed, lawdriven, regulated, enrolled, indoctrinated, preached at, controlled, checked, I estimated, valued, censured, commanded, by creatures who have neither die right nor the wisdom nor the virtue to do so ... .It is, under pretext I of public 'utility, and in the name of the general interest, to be placed under contribution, drilled, fleeced, exploited, monopolized, extorted from, squeezed, hoaxed, then, at the slightest resistance, the first word of complaint, to be repressed ... That is government; that is justice; that is its morality. (N ozick, p. ill) 33

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Whether the utopian vision is consistent with a minimal state or its antithesis is not to be solved but as the crux of the problematic condition of the American polis it is one of the forces behind the Prospects vision. I The second problematic condition is the tension between the political ideology of American society and its economic ideology. It is a question that not only enters at the production end, who owns and who decides, but also at the consumption end, what is I distributive justice, and is there an entitlement to certain economic goods and conditions? This itension between worker and owner, the corporation as a legal individual and individuals as members of corporations, wage labor, the necessity of continued economic growth, supply and demand functions, and so on, lead to I consequences of unemployment, alienation from personal economic wants and needs, powerlessness, poverty, and a totalizing vision of one mode of living and working the discipline of hierarchy, imposed behavior, and over consumption. It is a condition that was explored in two issues of Utne Reader, a bimonthly magazine of articles from the alternative press, in the following titles: "Why Work? When There's So Much More to Life" and ''For Love or Money Making a Living vs. Making a Life." ','The person who works right up to self-destruction is often accorded far more esteem ihat those seeking a more balanced life" (Moody, 1988, p. 65). "On the other hand---9r so they say-you're free, and if you don't like your job you can pursue happiness by starting a business of your very own, by becoming an 'independenf enh-epreneur. But you're only as independent as your credit rating. And to compete in business community, you '11 fmd yourself having to treat others-your employees-' as much like slaves as you can get away with" (Ventura, 1991, p. 78). 34

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This is the central expression of the contradiction between the powerless structure of economic discipijne and the "life" people seek to lead. I an alternative. The Prospects vision identifies anarchism as a positive political theory, j.e., not the negation of the state, but rather the existing civil society before the state its existence. For example, Hobbes "is aware that the state of I I nature in which there is no organized society is a logical fiction; it is the basis for the second fiction, the social contract" (Carter, 1971, p. 15). And I would add that the fiction of the state as a representative of the ''people's will" evolves quickly from the social contract ideal. The difficulty with the anarchism ideal is that for there to be any social decision-making there must be an aggregation of individual choices, which then constitutes the "people's will," and at that point we must have some structured system of aggregation and become susceptible to that system's physical and logical limitations. The identified then, is the closest feasible approximation to a functioning stateless Prospects als? identifies a syndicalist type of worker-owner agricultural and industrial production as an alternative. This would narrow the contradiction between work and other aspects of living by allowing a wide range of voluntary organizations whose benefits are to be reaped equitably. It also empowers everyone concerned with producti9n and consumption of the products of industry. This does not eliminate difficulties and dissatisfactions, but gives responsibility to all and legitimizes that decision-making. Factories will go out of business undoubtedly, but as a result of the aggregated decisions of everyone, rather than a few. This system cannot eliminate risk, only spread its share equitably. The alternatives identified then are to eliminate the state and wield authority through direct public and'frrm decision-making, and to devolve property to rights of use, not 35

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ownership, and all workers also owners at the level of the finn. The economic I vision differs from the political because microeconomic decisions need to be made at the microeconomic level. The mass public has a diminishing invesnnent in decisions I made in plants or on farms from which they do not consume nor prosper, and for which they do not work. Method for the alternative. Here is the core of the thesis and of the Prospects utopian vision, that in a mass, developed, industrialized society, information technology provides the means for aggregating the kinds of complex choices needed and implementing them with speed and accuracy, limited only by the logical limits of the aggregating process. The negative of the thesis is simply that in the absence of this technology there 1 are no identifiable feasible and functioning means to achieve the identified to the problematic conditions. This assumes that the I deinstitutionalization and disaggregation of current mass, developed culture is not feasible, as amply by the Chinese cultural revolution that failed not only in its ends, but by its totalizing means became the antithesis of the alternatives presented here. The Place of Technolo&Y What then of technology and its place in utopia? The products of the hand of people, techne, cannot fmally be separated from mind. The division between science and technology the result of utilitarian thinking that science, or knowledge in general, I must have some application, some action, to have value. That analytical utilitarian distinction itself has little value. Techne is always a product of the active mind; mind i and knowledge cannot be severed from their action on and in the world. In this sense, no utopia can a vision without a place for some level of technology, both 36

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social and physiCal. Historically, there have been two main responses to the place of technology in utqpia, those that trumpet the wonder of technology and those that trumpet its oppressiveness. "It is not until the seventeenth century that we find the beginnings of modem exaltation of complex technology" (Sibley, 1971, p. 17). In New Atlantis, Francis Bacon expresses the profound faith of the progressive nature of science and technology and the utopian future that a scientific society would have. This is the major vision of industrial society: as the conqueror of nature to carve out a human rational paradise within irrational nature. It is a totalizing vision of technology as the liberator of the race from original sin and its consequence, irrationality. "Gone is the notion of limits to what man can or ought to do with Nature. The idea of conquering Nature as an army would conquer another nation makes its full-fledged appearance and will have an enormous influence on the subsequent history of men's institutions and conceptions" (Sibley, p. 19). This view is intimately linked with the idea of progress as a linear, additive, upward sloping process of attaining the perfect society. It is also intimately linked with the capitalist industrial revolution and its ideal of unlimited material wealth and unlimited expansion markets. In this genre, technology is not merely the means toward a utopian Vision of society but the embodiment of that utopia-technology is the good. The otherresponse to technology in utopia has been "[t]he despair of dystopian writers about human capacity to control the technological process it has been initiated [leading] a few utopiasts in the last generation to formulate schemes which either halt technology at rather primitive levels or selectively encourage some types while prohibiting or restricting others" (Sibley, 1971, p. 37). In A. T. Wright's 37

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Islandia, a character defending the Islandian way of life expresses the view: ''Would it be pleasanter if we had come by train from the City?" (Sibley, p. 37). This embodies the anti-technological paradigm presented by many utopian and dystopian visions concerning not only the quality of experience that technology can provide, but the dangers of technology out of control, as in Mary Shelley's Frankenstein. Included in this genre are the dystopias antithetical to technology-as-the good where tec!mology-becomes-the-bad leading to Orwell's despairing conclusion of I 1984 where the ip.tegrity of the individual no longer exists. Human ambiyalence about technology will remain in any utopian vision and the Prospects vision uses the perspective called techno-structuralist, elaborated by Tehranian (Tehranian, 1990, pp. 212-217). In this viewpoint, technologies are neither good, bad, nor in and of themselves. ''This is because they developed out of institutional needs (in the case of information technologies, primarily military and business needs) and their impact is always mediated through the institutional arrangements and social forces ... (Tehranian, p. 5). In other words, technologies always feed into :the social and institutional paradigm and have good, bad, and neutral effects. It is the way that the paradigm uses and understands the technologies that will determine the greatest share of effect of that technology. In this view technologies feed into the institutionally created structures, magnifying strengths and weaknesses. The Prospects vision .takes three of the strengths of computerized information technology speed, logic, and memory-to overcome limits imposed by the nature of society and geography. It is the outcome of political will that will determine the characteristics of the technology that prevails. The overall conclusions of the chapter are that utopia, as a serious form of political theory, must conform to certain criteria to have validity. Those criteria include, but are 38

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not limited to, transformative possibilities rather than ideology and coherently linking means and ends. The Prospects vision presents information i technology as the central mechanism for meeting those requirements and I now focus on that 39

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CHAPTER 4 THE TECHNOLOGICAL ANALYSIS The Limits of Political Institutions Chapter 4 looks at the place of information technologies in political structures. Technology has its own internal logic and limits that must be explored both outside of I and in relation to :the political structures it will serve, yet in a way that is non-deterministic. And beyond limits and logic, it also explores technology as a process and its possibilities of meeting the process needs of the Prospects vision. It has been sal.d that economics is the science of scarcity, as all the principles and analyses that spring from the dismal science are based on an assumption of limitations, limited resources, labor, capital, and land. In an analogous way political science is the science of and decision-making limitations and the power structures that result There are basic identifiable variables that enter into the portrait of political limitations. One is population of the decision-making group. The number of members of a political body will influence other variables, namely, the amount of land needed to produce food, geographical distance between any two individual members and their communities, farr:rily size and structure, ability to assemble and travel, time needed for communication between members and communities, and types of aggregation/counting mechanisms that can be used. All of these variables interact and affect one another on one side of the equation, but on the other side is the resultant political system that must live within the lirtrl.tations of the variables as a whole to be feasible and functioning. One of the most often cited examples of this qualitative equation is the limitation of clirect democracy in mass societies because of geographical and physical constraints.

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I You simply cannot cart off everyone in the society to a mass meeting, and if you could, you wouldn't have a large enough building to house them, nor enough time for universal participation. This basic limitation of reality in economics is referred to as the Production Possibilities Frontier (PPF), basically a zero-sum equation with two or more variables. An increase in one, say production of televisions, necessarily leads to decrease in another, artichokes, because capital, labor, and material are limited. Again, we can create an analogous example in political science calling it the Institutional Possibilities Frontier (IPF). You simply cannot create a feasible, functioning institution that requires more personnel, information, or time than it has. One of the of the limits in the PPF and the IPF is technology. A restructuring of capital into a technology that uses the same labor and material more efficiently can raise the PPF and IPF to new limits. It is imponant to point out that limits are not eliminated, but simply redefined at a new level. An economy can perform below the PPF limits, but if maximum production is a valid good, then the situation is not optimal. And again, a political system can also perform below the IPF, but if maximum participation and freedom of the individual are valid goods, then that situation is also not optimal. I Oyercomine Limits: Requirements for Democratic Technology It is the contention of this thesis that while representative democracy may have expressed the outermost limits of the IPF at an historical point in time, that is no longer the case. Technology, specifically, information technology, has pushed that IPF outward and the current political system is functioning suboptimally. Information technologies proVide the necessary means for a mass, developed society to meet, 41

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discuss, and decisions with little regard to geographical, transportation, or population Tehranian (1990) states, At thb risk of oversimplification, however, let me conclude that information technolowes can in fact serve a more democratic world development on at least the follo'Yffig three conditions: First, if they are made more interactive. Second, if they achieve more universality and accessibility. And third, if they are increasingly locked into participatory, democratic institutions and networks. (p. 17) i Some of the first steps toward interactivity have taken place on various scales in several countries. with television and cable. The Qube in Columbus, Ohio, was one such system that provided : interactive responses to viewers who were connected to a main computer at the I I television Not only were preferences recruited directly but also time spent watching television, channel choices, and so on, were recorded by the central computer. The system was instituted in several major cities in slightly different formats. The sysiems offered entertainment, education, public opinion polling, I teleshopping, community interaction. By 1984, however, Warner Amex, owner of Qube, was askink to be released from its agreement under cable regulation. It wasn't the technical of the system but rather a technology quickly out of date and low community participation that led to heavy fmanciallosses. (The Economist, January 28, 1984, p. 27, cited in Tehranian, 1990, p. 127) The Qube seems to have come to ... interactive social dialogue was when in deference to its community obligations [under regulation agreement] it offered channel facilities at no cost for 'town meetings' ... The Commission asked a senes of questions on which the citizens gave their preferences. Results were displayed within seconds after they had pressed the buttons. To make sure of the freedom that comes from anonymity of response, the Qube hosts assured the respondents that the computer had been set in a mode that would noi identify them. Asked if they wanted to do the experiment again, 96 percent pressed the Yes button, and within 10 seconds the computer, having worked out that percentage, relayed it to the home screens. (Tehranian, 1990, p. 127) 42

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The National Science Foundation also sponsored experiments in several U.S. cities to explore possibilities of the mostly unused two-way interactive potentials of cable television (CATV). A project in Reading, Pennsylvania, tested the audio/visual conferencing for providing social service programs to the elderly. A Rockford, lllinois, project applied CATV to in-service training for a single occupational group, firefighters. Anda Spartenburg, South Carolina, project offered formal education to students in their homes. The initial findings were that, at least technically, all the projects were technically feasible and functioned as projected. (Kaiser, Marko & Witte, 1977, pp. 16-23) Such experiments have been conducted in many parts of the world, especially in Japan, Europe generally, and (West) Germany. In Berlin, the Heinrich-Hertz-Institute (HHI) provided interactive cable services to subscribers that included town planning, social services, to authorities, tele-education, purchases of goods and services, and entertainmeq.t Such a contracted service, available in 1977, proves not only the technical feasibility of such a system, but also its applicability. The mn system is close indeed to the system discussed in the Prospects vision, although the Prospects vision I downplays the entertainment and "television" potentials of such home/workstations. The structure of the system tested relates directly to its function. An interaetive two way cable system feeds into the centralizing character of computer information technologies. Here, users can only interact with the center and receive information from that center. This gives the power of information and control to the center and is only made available from the center. This concept of "dumb" workstations dependent on a i central mainframe computer would not be ideal for creating a world like the Prospects vision. Here, decentralized "smart" workstations that can communicate with a central 43

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I computer, or central computers, and are also capable of point-to-point I communications :with any other workstation, would be desirable. One of the political applications of computer information technology in the U.S. was in government. "Urban government can be viewed as an information I system in which pata are collected, organized, stored, managed, analyzed, and i retrieved-all ultimately for decision-making purposes" (Westin, 1971, p. 331). The application of in areas such as urban government in fact created fields of study such as systems science and information management. While many had hoped for a total design and implementation, as with most new technologies, computers were integrated piecemeal and a great deal of information duplication and confusion occurred. I think it is important to stress here that even with about 30 years of integration of technologies in the urban management area, no cities have i yet achieved an integrated and "total" systems operation. It is also important to note that this use of infom1ation technologies so far has only served the bureaucracies and I I officials already institutionalized by urban government; it has not served to open urban I government to the public, nor challenged the basic ways in which U.S. urban centers I do business. If rutything, it has allowed urban centers to increase in population to the size of many snuill countries and still maintain the established order. Some form of I computerized vote tallying has been implemented in almost every local voting precinct, yet again the method of voting has changed little, only the speed and accuracy with I which the has been performed. We are an automated and automating society. I do not think it is at this point to state that the integration of information technologies to date has tended t6 feed into the current institutional political and economic framework by strengthening; rather than challenging it. The most trivial use yet put to computers 44

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has been in where they remain isolated devices with programs to store recipes and addresses or 'produce computerized entertainment But the important question does ' not concern critique but why this this so. Part of the answer lies in the ideologies of technology that are presented "[T]echnophiles tend to be the optimists who believe that the present revolution in information storage, processing, and retrieval has already inaugmated a 'post-industrial, information society' with higher productivity and plenty at the world centers that will eventually trickle down to the peripheries" (fehranian, 1990, p. 4). According to this view, information technologies have already done what they best, by making present systems more.efficient. Returning to Mannheim, even;though most of these portraits of future techno-society couldn't be classified as utopjan, the future they portray has little revolutionary potential. The technologies have deterministic qualities and not surprisingly those qualities tend to be the capitalist/indqstrial and representative democratic ones already in existence. This is ideology. Another perspective that tends to feed into the present institutional framework is the i techno-neutrals : .. "who have few theoretical pretensions and considerable interest at stake not to their clients" (Tehranian, 1990, p. 5). These are the consultants and engineers who according to the needs of the institutions they serve. This is also a reflection of the corporatist employee status of most engineers and information processors. The fustitutions they work for do not demand nor desire revolutionary ideas. This "non-ideology" is also ideological according to Mannheim's (1956) analysis because it also serves the interests of the classes and structure as they exist. The answer also revolves around economic structures. The Prospects vision society would require an 1enormous capital investment in information technology to meet the second of Tehranian that they be made universal and accessible. The 45

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revolutionary democratic potential in the workplace and society is a damper to most I current to invest in such a large capitalization project They may be putting I themselves out of business and restructuring social and economic power in unpredictable and uncertain ways. Most capital is controlled by corporations or by governmental units through taxation. As discussed above, urban governments have defined the public good as an investment in information technologies that will make their functions easier and more efficient, not a decentralization of power to direct voting. Analogously, corporations have not seen information technologies as a worker empowerment tool, but one that could make them niore efficient The first application of multimillion dollar, room-sized computers that could do little more than hand-held calculators today was accounting and payroll. The effk;iency of billing and ordering represented an enormous long-term savings and increased earnings for the corporation. Who will pay? It will have to be I individuals who are invested politically and economically in universal and accessible information technology. The third requirement of Tehranian is that information technologies be "locked into participatory, democratic institutions and networks." Two examples of experiments in the participatory yein are televoting ... a novel method of public opinion polling originally by Vincent Campbell as a new public communication system for the San Jose Unified School District in California" (Tehranian, 1990, p.112). In 1918, Ted Becker, Richard Chadwick, and Christa Slaton of the University of Hawaii revised the San Jose Televote in order to turn it into a scientific irandom public opinion sample of a population. In contrast to conventiQnal public opinion polls, however, the new Televote method attempts to inform the public before sampling their opinions. Following a random selection of Televoters, they were provided with brochures on the issues at stake. Ample time is allowed for the reading of these materials before the 46

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Televote staff calls up the voters to ask for their responses. (Tehranian, 1990, p. 112) A New Zealand televote in 1981 also surveyed a sample population on the future of New Zealand and encouraged televoters to make some difficult choices among four different futures for their country. (Tehranian, 1990) While televoting is another example of the application of information technology, it was basically as another method Qf random-sample polling on certain questions, which of course suffer from the same biases as any survey. Also, the televoting is center-to-point, not point to-point, so that the bias comes directly from those at the center and cannot be overcome by poipt-to-point debate and communication. The voter doesn't set the I agenda. Paul Goodman spoke to this question of the place of technology on that Institution Possibilities Frontier discussed above in "Can Technology Be Humane?" I need hardly point out that American society is peculiarly liable to the corruption of inauthenticity, busily producing phony products. It lives by public relations, abstract ideals, front politics, show-business communications, mandarin credentials. It is preeminently over technologized. And computer technologists especially suffer for the euphoria of being in a new and rapidly expanding field. It is so astonishing that the robot can do the job at all or seem to do it, that it is easy to blink at the fact that he is doing it badly or isn't really doing quite that job. (Teich, 1990, p. 243) I If the televote is just an extension of opinion polling and the technology is really doing a poor job compared to its potential, then what are the possibilities? Tehranian discusses how ... information technologies, no matter how interactive, cheap, or accessible, do not by themselves lead to democratic formations. The latest [1984] U.S. census data demonstrates the point well. (1990, p. 236) ... the Bureau of the Census has confirmed the suspicions about a widening gap between information-rich and information-poor. According to this report based on a survey conducted in 1984, some 15 million American adults had computers at home, but only 53 percent used them. Predictably, 'the figures also suggest the creation of a computer elite based on race, sex, and income. 47

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Only about 3.4% of children in households with annual incomes of less than $10,000 bad a computer at home, compared with 37% of children in families with of $50,000. Of those who had them, boys were more likely to use a con;tputer than girls (80% to 66% ), and among adults 63% of men used computers at home compared with only 43% of women. As for race, 17% of all white chijdren used computers at home, compared with 6% and less than 5% of black and Hispanic children, respectively. (The Economist, April23, 1988, cited in Tehranian, 1990, p.156) I In contrast to privately owned or governmentally operated information media systems, Tehranian discusses several characteristics of what he would consider a I communitarian system, all of which I believe are evident in the Prospects vision. They are community ownership and management, deprofessionalization of programming and production, empowerment of audiences, interactive technologies and networks, decentralization, cultural and structural pluralism, and thinking globally, acting locally. The implementatjion of the Prospects vision would not come about because of some I I deterministic quality of information technologies. It would not become a dystopia through those same qualities, but rather would be implemented through the political and economic struggle of those who would want to restructure institutions to take advantage of the speed, logic, and memory capacity of information technologies to expand the IPF to include mass, developed anarcho-syndicalist forms. The Logic of the System Having analyzed the place of information technologies in a political context, I now tum to the limits of the speed, logic, and memory capacity of information technologies themselves and the boundaries that creates for the design of institutions. The Baconian i view of progressive science as a limitless enterprise of gathering knowledge to eternally better the human condition was probably most symbolically overturned by the dramatic logic and subsequent experimental verification of Heisenburg's uncertainty principle in 48

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physics. (Heisenburg's uncetainty principle is a mathematical relation that demonstrates that if an locates the exact position of a subatomic particle, the speed cannot be exactly; and conversely that if speed is determined exactly, then location can only be estimated. This is not a limitation of the experimental apparatus, but a limit imposed by nature.) That the very reality that had so cheerl'ully given its secrets to the scientific method would also impose ultimate limits to knowledge pulled the foundation from progressive natural science. In a similar way, Arrow's impossibility theorem within the context of general social choice theory pulled the foundation from under progressive social science which held that once you specified a set of preferred criteria for the good society, only implementation remained. Arrow specified a set of desirable and consistent conditions and discovered, "It is not just that it is difficult to a social choice rule that satisfies all these .... No, it isn'tjust that it is hard; it is impossible" (Kelly, 1988, p. 80). The tension is between the individual and aggregation of individual preferences I (wants and need$) into social decision. This can also be complicated infmitely by unanimous subsets of individuals aggregating subset preferences into society. To maintain some simplicity, I will assume only the tension between the individual and the aggregation of preferences and its application in the Prospects vision. Society then is merely the aggregation of individual preferences into some form of communal action. The crux for the information engineer, according to Arrow's (1970) theorem, is that there is no software program, no technological breakthrough that can overcome the logical limits of the non-existence of a social choice rule that will simultaneously satisfy all the desirable conditions of a social system. The principle tenet of social choice theory and economics from which it sprang is I the assumption Of a rational actor and rational choice. Certainly many fundamental 49

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social science can be attacked at this foundation level by denying (subject to proof) that iri fact that assumption is untenable. For the purposes of this thesis I don't believe there need be any further exploration of this question. The actor can be rational or irrational as dm the social outputs resulting. My primary concern is with the means of aggregate choice, and that means must always conform to some rational structure. In fact it is more applicable in the realm of information technology and social choice progranuning, because those must be expressed in rational structures that can be processed with technology that conforms to its own rational limits, e.g., at present the limits of binary information coding. The first of the resulting analyses of democratic fonns based on the rational assumption is the contradictions of majority rule. Arrow states, "When I fli'st studied the problem and developed the contradictions in the majority rule system, I was sure that this was no original discovery" (1970, p. 93). In fact, this had been discussed historically by Condorcet, Borda, Laplace, Nanson, Galton, and others. The simplest explanation of this problem is that ... there is not a unique way of extending simple majority voting ,to make decisions among three or more alternatives" (Kelly, 1988, p. 15). For exampl:e, three people voting on three possible alternatives (x, y, z) can end in a situation where their preferences are ordered as the following: 1: xyz 2: yzx 3: zxy In this situation, if we aggregate by Condorcet winning pairs, on the fli'st count x is preferable toy (no. 1 and no. 3 would prefer x toy); on the second county beats z (no. I I 1 and no. 2 prefer y to z); and on the third count z beats x (no. 2 and no. 3 prefer z to x). In other words there is no winner with this vote of preference ordering. This method for aggregating individual preferences among three individuals with three 50

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alternatives can lead to a situation where the logic of the system produces no aggregate decision even each individual is clear in preference. And Arrow's impossibility theorem tells us there is no system with a set of conditions that can aggregate individual preferences into a social choice meeting all the conditions. This doesn't mean that there are no methods for getting around this difficulty in the system, only that the difficulty will always remain. How then are democratic systems to be designed to confront these aggregation limits? A second related question also needs to be asked. What if the system does work and there is a majority victor? What are the consequences for majority rule? If one of the conditions (as it is in Arrow's theorem) is that there be no dictator (and in this thesis more generally, wielder of authority) can the majority act as a dictator? It is a long and well debate4 idea that in direct democracies the majority can treat the minority tyrannically. "As I argued ... the principle of majority rule entails, at the very least, that if one of a set of feasible alternatives is the first choice of a majority of voters, then that alternative ought to be chosen" (Sugden, 1981, p. 176). Majority rule is certainly the key procedural attribute of a democratic system, but it does not follow that where there is majoritY< rule there is democracy. First, it is evident from the contradictions of I majority rule that there are instances where the system simply exceeds its logical limits and cannot produce a social preference aggregate that also corresponds to the preferences of the individuals who voted. Second, there are circumstances where the above rule expressed in Sugden "if there is a majority, the first choice of that majority prevails" as. the aggregate of the individual preferences simply is not the "will" of the majority. And it, is this moral claim that a majority expresses an aggregate social will that gives demoeracy its political force. For example, 51

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A community of 1000 people is made up of two villages, A and B, which are severhl miles apart The question at issue is whether licences should be given to 8llow [pubs] to be set up. A majority of the 600 inhabitants of village A are drinkers; in village B, a majority of the 400 inhabitants are abstainers. Drinkers.are in favour of pubs while abstainers object to the associated noise and traffic. There are four alternatives: that pubs should be licensed in both villages (w), that a pub should be allowed in village A but not in B (x), that a pub should be allowed in village B but not in village A (y), and that no pubs should be allowed in either village (z). The profile of preferences is: 1-450: (w,x,y,z); (z,y,x,w); 601-750: (w,y,x,z); 751-1000: (z,x,y,w). Voters 1-;600 live in village A and the rest live in village B. Alternative w, that pubs be allowed in both villages, is the first choice of a majority of the whole community. (Sugden, 1981, p. 177) In this example, a pub, to which a majority of residents of B object for their village, is imposed by a majority of overall aggregated voters. There are also other examples of alternative methods to just simple majority rule, e.g., qualified majorities, log-rolling. But I don't want, to stray too far from the main point, which is the question of whether i I the Prospects is simply another form of expanded representative democracy with the majority a tyrannical wielder of power and authority rather than the representative state machinery.' One way out of the morass is the way pointed by what Arrow ( 1970) calls "extended sympathy" and in the context of justice by Rawls. That is essentially to be able to "put yourself in someone else's shoes" or blind institutional roles. How would individuals act, and how would it affect the preference ordering, if they did not know what institutional role they would fill. "It is exemplified, in perhaps an extreme form, by an inscription supposedly found in an English graveyard. 'Here lies Martin Engelbrodde, I Ha'e mercy on my soul, Lord God, I As I would do were I Lord God, I And Thou wert Martin Englebrodde" (Arrow, 1970, p. 114). This is the case in the Prospects vision where the aggregation of individual preferences is tllrough a diverse system of smaller voluntary units whose aggregating I I systems vary, rather than through a totalizing single system of aggregation. For 52

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example, the jury in the Prospects case was chosen by random selection as was the second presenter, the first presenter volunteered based on merit and was accepted by the case committee that the city had formed. The judge was chosen by community election, and the whole process was overseen by all the individuals who had immediate and realtime and also later-time access to the case. The lack of a totalizing system does not guarantee that the limits of aggregation will not appear in some failme to match the aggregate to preference, but it does guarantee that that limitation will not appear because of a totalizing system. The potential for consensus exists because workstations are point-to-point and preferences can be changed, rather than simply counted. When would consensus be an adequate substitute for authority? An organization whose members have identical interests and identical information wiU be one in which spontaneous consensus would be efficient; each member would correctly perceive the best decision according to his interests, and since the interests are in common, they would all agree on the decision. In face-to face groups, it may be possible to interchange information cheaply enough [italics added] so that the identity of information can be achieved, and if the I group has a sufficiently overriding commonly valued purpose, the identity of interests may also be a valid assumption. (Arrow,l974, pp. 69-70)2 The fmal. sanction on majority tyranny, however, is the legitimization of the secession of individuals from any system. While that is true of every political system, usually called reyolution, the cost for secession is usually so high that suboptimal functioning is often preferable. On the other side, concerning the lack of stability and opportunity cost of constant change, there are also simple physical limits to the number of secessions an 'individual can withstand, whether there is an external authority or not. 2 I would extend: this definition of face-to-face groups due to the technological expansion of the geography/information limits discussed on page 38. 53

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The Prospects vision also works because the "extended sympathy" requirement can be met by random selection for the short-term institutional roles necessary for functioning. Why would a person act justly, according to Rawlsian analysis. when it is only a moral question? Make that moral question a reality, however, by randomly choosing roles and the justice is evident (Not that this would guarantee that an individual would act justly in that role, only that this is the best way to make the attempt) Authority and Indiyidua1 Choice I am left with two central questions to explore, the problem of authority in the Prospects vision expressed by the court judgment, and does random authority have any greater moral claim than institutionalized authority. The problem of authority in the I Prospects case expressed by the defendant character, Sharon, "By your own beliefs how can you enforce such a judgment, a verdict? How can you justify the coercive intrusion into my life and welfare and how will you enforce it except by physical force? ... For you will have to destroy your society to enslave me and control my actions and vrords ... You will end non-authoritarianism and the lack of a state i with me. or I do it for you." Can the court assume a position of authority and enforce its decision for the lifetime of the defendant without destroying the anarchistic society of radical equality it values? Radical equality does not eliminate the human condition of authority arising in any cooperative effort. What it does presume is that authority will be shared and equitable and will not crystalize into status quo institutional forms where individuals attached to certain roles become constant over time. If all individuals have 1the same opportunity and responsibility to wield social authority over time. personal authority and freedom can be maintained while the social authority is 54

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shared equitably. The intrusion into the defendant's life is justifiable because to do so retains the form of power distribution, whereas a lack of intrusion solidifies the absolute authoritative claim of the defendant over that equitable distribution. Does randomly distributed authority have any greater moral claim than institutionalized Smith and Ricardo both demonstrated the superiority of specialization, and how, -through trading specialized goods at certain rates of exchange, both parties ende4 up gaining in valued goods. Apply this analysis to the political function of wielding authority. Can two or more individuals be better off by specializing, some in wielding authority, some in yielding it, than both individuals retaining rights td authority? A more technical and complete restatement is useful. The generalized Hobbes argument [that in the absence of authority, there is a "war of each against all," and as a result, "the life of man is poor, nasty, brutish, and short."] presupposes two elements: the superior productivity and complexity of joint production, and the cost of interchanging information. (Arrow, 1974, p 56) In the Prospepts vision the capital investment has been made and the cost of interchanging information lowered to the point that the authority argument is negligible. The question then remams whether the ceding of an individual's (x) authority to another individual or grohp (y) would result in superior productivity and a protection of all individuals greater than if they operated separately. H so, the rational individual would prefer to cede personal authority to others to receive a net benefit. This argument assumes that it is a rational choice that is available. It is also a result of speculation about the arising of unequal authority in the form of institutions and the state. This is the importance of the myth of the social contract. It assumes that because there is unequal authority and the institution of the state exists that rational individuals have signed the contract and found a net benefit in doing so. But where is an 55

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individual to be fomtd who has signed the contract? Where is the person hiding? In fact, we are. all sckialized into the political systems of power and authority without ever being asked to rationally evaluate and "sign-on." What of an individual who wishes to "sign-off' the social contract? The person is no less subject to the political system of power and authority than before and often also loses personal freedom. Thus the state, and systems of authority, as we are socialized into them are coercive. There is no rational choice in fact, only revolution. A rational individual then, it is my contention, would find a system of random, equitable authority where the social contract was a real device and could be "signed-on" or "signed-off' to have a higher moral claim than a system of institutionalized authority where no such rational choice is possible. If the institution were non-coercive and allowed individu.als to "sign-off," then I would argue that the rational individual would be indifferent to the two systems because individual authority would be retained under either. The non-coercive state is more of a perfected vision of utopia, requiring assumptions of the perfectibility of human beings, than the Prospects vision, requiring no such assumpt:ion. ''The polar alternative to authority would be consensus .... By consensus I any reasonable and acceptable means of aggregating individual interests" (Arrow, 1974, p. 69) . . some of us who have read a little bit of the history of thought have heard of anarcho-syndicalism before. Bakunin and Sorel had spoken to the same point many years ago. But it is a real one. There is a demand for what might bel termed sincerity, for a complete unity between the individual and the social roles ... (Arrow, 1974, pp. 15-16) I This chapter1has focused on the limits and potential of information technology in the Prospects vision as both transforming and functional. The argument that is presented is that at a minimai level, where no transformation of systems take place but only novel 56

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fonns of process in the same system the Prospects vision still increases the level of individual freedom through non-coercive participation. The question that remains is what model of transformation would best serve maximizing individual freedom with technology as the process means. 57

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CHAPTER 5 THE ANARCHO-SYNDICALIST FOUNDATION The Anarchist vision Chapter 5 explores anarcho-syndicalism as an appropriate utopian model made functional and feasible through information technology processing. The historical difficulties of the model are presented and questions central to it, authority, property, and non-coercive decision making, are presented. The first difficulty in discussing anarchism in general is that there are many I anarchisms. Like' the many socialisms that were part of the international movement, anarchist has produced collective, radical individual, peasant, pacifist, violent, communist, conspiratorial, and many additional minor versions of theoretical and activist ways to the stateless, cooperative society. Unlike socialism, anarchism has not undergone an analogous open debate and, frankly, open warfare to distill the theory into what is workable or winnable. There are also very few models of anarchist development, of in the real world anarchist societies can confront the day-to-day concerns and of a community. This strikes both ways. Anarchism as a critique is powerful because of its theoretical diversity and purity from problems of application. But that same lack of application and historical precedent often gives the I critique little validity. The many anarchisms share the quality that there is no institutional means of coercive enforcement of authority; that does not mean that there is no social order or organization. I want to be qlear on a point. There are numerous examples of anarchist or anarchist-style communities and cooperative efforts. Michael Taylor in Community,

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Anarchy andLib'eny (1982) discusses anthropologically-based descriptions of anarchistic communities that include acephalous societies, centralized redistribution systems, and and big-man systems. Acephalous societies (literally, no head) have almost no political or economic specialization and what does exist is ad hoc concentration of authority that flows continuously throughout the membership. I Centralized redistribution systems have crystalized authority around various hereditary or divinely sanctjoned leaderships,.but that authority is under obligation to be used for the benefit of all (usually in the form of provision of large feasts). Non-leaders have more claims on leaders by virtue of their position thari is true of the reverse. Chiefdoms and big-man systems have considerable inequality of prestige and authority which again in large measure, depends on merit and generosity. Taylor includes peasant and intentional communities as examples of anarchistic organization as well. The critical attribute shared by all these systems that Taylor presents is that they have no formal, legitimate means of enforcing what functional authority they may have. That authority is always in. flux-: in effect, there is no state. The theoretical exploration of the state arising as in Hobbes' work resorts to speculations on the "state of nature," a state that transparently did not exist, or if it did was extraordinarily short lived because of undesirability of the "war of each against all." This view assumes the continuity of the state form of coerced social welfare from time immemorial and ignores the very process of the state arising from non-state communities that it purports to explain. "During almost all of the time since Homo sapiens emerged, he has lived in stateless, 'primitive' communities" (Taylor, 1982, p. 33). The Kung! of the Kalihari have in fact maintained such societies up to modern times. The diffi<;:ulty is not in the existence of feasible, functioning anarchist societies but their scale. The crucial question is can this form of organization exist in mass, 59

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developed societies? Authority embodied in the political state and the economic authority of a is the issue surrounding that question. We are communists. But our communism is not that of the authoritarian school: is anarchist communism, communism without government, free communism. It is a synthesis of the two chief aims pursued by humanity since the dawn of history-economic freedom and political freedom ... The means of prcx:luction and of satisfaction of all needs of society have been created by the common efforts of all, must be at the disposal of all. (Dolgoff, 197 4, p. 29) The Syndicalist Vision The econotru:c authority is ignored or dealt with cursorily in many of the anarchist perspectives. Some perspectives, for example, peasant anarchism that idealized the life of the European }>easant advocating withdrawal from the state to mutualist agricultural societies, are si111ply inappropriate for exploring the place of anarchist ideas in mass, developed society. For this reason, and because syndicalist organization at the level of the firm can potentially deal with contradictions between micro-and macroeconomic decision-making, anarcho-syndicalism makes the most sense as a vision of liberated mass, developed society . . the anarchism practiced and preached by a radical trade unionism proved of a sounder variety. It was frrst and foremost based on the realities of nineteenth century European life; and drew its support from the struggles between classes that was at the center of the historic drama. As one writer put it: "Anarcho-syndicalism is par excellence the fighting doctrine of the organized working class, in which the spirit of enterprise and initiative, physical courage and the taste for responsibility have always been highly esteemed." (Horowitz, 1964, p-:35) Syndicalism in the form of worker-owned and operated frrms is no mere theoretical construct Numerous variations on this theme provide models for approaching empirical questions of how such frrms operate, and how they can be constructed to be 60

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efficient and competitive. Examples of long-term, successful worker-owned firms include Plywood Co-ops in the U.S. Northwest, Mondragon in Spain, the socialist worker-managed industries in Yugoslavia, and many smaller and diverse, yet no less important, firms across the globe (Zwerdling, 1984). But the anarcho-syndicalist version of worker agitation and control was less clearly successful. The theoretical expansion of anarcho-syndicalism from a narrow class-based tool, "the fighting doctrine .of the organized working class" to a direct economic and political struggle to mankind from the state by Fernand Pelloutier and others, makes of it an appropriate critique of the state and institutionalized authority, not just another analysis of class-based political theory. Yet a renewed use of anarcho-syndicalist theory in this thesis reqres some speculation and addressing of the historical reasons for anarcho-syndicalist failure. Horowitz in The Anarchists (1964) identifies three problems: 1) They tended to approach socialism as a reality around the comer, rather than a long-rang process of social reorganization. (Lack of principles or program.) 2) They abandoned the task of organization. 3) They failed to offer sound sociological or psychological reasons for getting people to act. It failed to distinguish between the ends of action and the stimuli to action. I would add that they also lacked the technical means for organizing the society envisioned in the absence of the state. Engels in his On Authority criticizes the "anti-authoritarians" strongly on the grounds that they assume the new society is about to be born, full-grown, like Minerva from the head of Zeus. Authority, Engels argues, is just what the new society needs (Marx, Lenin, & Engels, 1974, pp. 100-104). What Engels fails to realize in his critique is that the "anti-authoritarians" or anarchists of which he speaks are criticizing the principle of l;!.Uthority on the same basis, namely that a revolution that maintains the state principle of authority gives birth to another state born, full-grown from the head of 61

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the old. How then can anarcho-syndicalism develop a program and principles? The moral imperative is the historic drive toward freedom and equality; it is not rational for an individual to choose less autonomy than human capacity allows, and even if an irrational individual did make that choice, there is no imperative other than coercion preventing a of that choice. The fairness imperative is the opportunity cost of coercion, a cost that has become clear in one arena through the arms race and vast sums of money spent on standing armies across the world. The practical imperative is the continual and long-standing abuses of life and liberty that states act out from political detention to the holocausts of millions. These principles become program when a I means is providect to achieve the anarcho-syndicalist vision, a program that includes feasible, functioning worker-owned and managed firms, expanded use of direct democratic folll1S (initiative and petition) toward anarcho-syndicalist aims, application of technology information gathering and decision-making, passive resistance to state authority, and so on. Horowitz's frrst cause of the collapse of anarcho-syndicalism historically does not imply that there can be no program or principles as this example I hopefully illustrates. Secondly, the task of organization is one that must occur through the active integration of means to ends. This is Horowitz's weakest point because the anarcho syndicalists did not believe they had to organize because historical development would lead their direction. To say that anarcho-sydicalists failed to organize because they didn't organize is a bit redundant. Yet, I accept Horowitz's point that the failure was not in their lack,of organization but their belief in the inevitability of historical development Thirdly, there is more than enough "stimuli to action" to analyze since the writings of most anarchists around the time of the French Revolution. The modem technological 62

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state has used coercive and destructive force on scales unimaginable to monarchs and radicals alike. The struggle to constrain state power in the twentieth century has taken an international statist form, however, in the United Nations and other international security organizations, rather than in a restructuring or abolition of the state itself. And, fmally,.the means for mass point-to-point communication and mass I aggregation of inllividual preferences is available and technically feasible. "A liberated society, I will not want to negate technology precisely because it is liberated and can strike a balance" (Bookchin, 1971, p. 134). I do wish to belittle .the fact that behind a single yard of high quality electric wiring lies a copper mine, the machinery needed to operate it, a plant for producing insulating material, a copper smelting and shaping complex, a transportation system for distributing the wiring-and behind each of these complexes other mines, plants, machine shops and so forth .. .let us grant that copper Will fall within the sizeable category of material that can be furnished only be a nationwide system of distribution ... This distribution system need not require the mediation of centralized bureaucratic institutions. (Bookchin, pp. 137-138) PrcmertY and Law The mediation necessary in place of centralized bureaucratic institutions that wield coercive authoricy is provided for precisely by the anarcho-syndicalist vision. What of property in that vision? The analysis of the origins of property and the origins of the legitimacy of property by many political philosophers is usually rooted in the same "state of nature" fiction as the social contract and the arising state. The difficulty with such an analysis is that the individualist definition of property (as land staked out and mixed with labor for survival resulting in a legitimate property claim) I does not correspond with the world into which we are born. Here there is no unclaimed land, no stakes left to put down, and a system of state sanctioned property rights that 63

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' extend far beyond survival needs. Property is a legal claim on capital, land, and labor that can be obtained, extended, voided, and created by other legal means-with the state as the coercive authority to back the claim. Proudhon claims in Property and Revolution that is robbery .. Such an author teaches that property is a civil right, born of occupati0n and sanctioned by law; another maintains that it is a natural right originating in labor .. .I contend that neither labor nor occupation, nor law, can create property; that it is an effect without a cause" (Horowitz, 1964, p. 87). He also discusses in The'General Idea of the Revolution in the Nineteenth Century that The people, even those who are Socialists, whatever they may say, want to be and, if I may offer myself as a witness, I can say that, after ten years of careful examination, I fmd the feelings of the masses on this point stronger and more resistant than on any other question. I have succeeded in shaking their opinions, but have made no impression on their sentiments .... that the tpore ground the principles of democracy have gained, the more I have seen the working classes, both in the d.ty and country, interpret these principles favorably to individual ownership. (Proudhon, 1969, p. 210) Property, or ownership, in this version differs from the legal entity by being based on personal use,: rather than speculation. The state simultaneously sanctions certain forms of speculative property claims, when it strengthens its authority interests, and outlaws other fdrms when it threatens those interests. Proudhon s basic conclusion for the use and disposition of property and social goods is by contract rather than law. Rather than tangentially explore the idea of non-state contracts as legitimate where law I is not and its relation to property ownership, I will simply reflect that the Prospects I vision makes use of this idea of individuals voluntarily entering into community contracts that decide the disposition of property within those communities. That disposition could vary from community to community. It is assumed that under these conditions the djsposition of grandiose speculative property claims would not be in the 64

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best interests of the individuals of the community and would not arise without the authority of the to enforce those claims. The complaint is then often raised-what of monopolies? price fixing? cornering the market? Are these not legitimate limitations on the free market that without state authority would develop out of control? Here we must remember that what the state is controlling is its own creation, namely the legal entity of the corporation with recognized rights and duties that the state uses its coercive authority to protect Monopolies and price fixing are the products of the state and its corporate creations, not the free market. I Non-coercive Social Decisions I The "tragedy1 of the commons" probably best describes the "free-market" concern between public welfare, the commons, and individual rational self-interest. The argument is set out by Garrett Hardin: A pasture is open to all. The village shepherds keep animals.on the commons and each is assumed to be maximizing his or her own gain. As long as the common pasture capacity can handle the number of grazing animals, a shepherd can add an extra animal without affecting the yield of his animals, others' animals, or the sustainability of the common pasture. However, at that limit the shepherd will have a gain and a loss from adding one animal. However, the net benefit of added milk, meat, etc., accrues to the shepherd while the loss is spread over all the shepherds. In this situation it would be rational for the shepherd to continue adding animals, as net gams would continue to accrue, and the shepherds collectively, all acting in their best self interest, could destroy the ability of the pasture to support livestock at all. Abstracted, this problem becomes a game known as the Prisoners' Dilemma found in Games and Decisions by R. Duncan Luce and Howard Raiffa and reiterated in the 65

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political context by Michael Taylor in Anarchy and Cooperation (1976). Two individuals have a choice of two courses of action. The two individuals must choose their strategies at'the same time, or in complete ignorance of the other's choice. Associated with each pair of choices is a payoff based on four variables all of which are related with decreasing value. Graphically, this would appear as the following matrix: Individual 2 ....-1 c D c 'tl X,X z,y .... > D '..5 y,z w,w where y>x>w>zi rows are chosen by individual 1 and columns by 2, and the first entry in each cell of the matrix is the payoff to 1, the second to 2. Each player would obtain a higher payoff if he chooses D (Defect) rather than C (Cooperate), no matter what the other player chooses. However, by choosing D, each player gets a payoff w. A choice I for strategy C would have yielded each player a payoff x, where x>w. We defme a Pareto-optimal outcome as one where no other outcome is strictly preferred by at least one player. An outcome that is not Pareto-optimal is Pareto-inferior. The dilemma is, of course, that the rational choice for maximizing individual welfare (getting payoff y), leads to a Pareto-inferior outcome for both players together. Rational individual choice cannot be aggregated into mutual welfare in this game. Even if the individuals could communicate, is no incentive to keep the agreement because defecting from the agreement would lead to a higher individual payoff. Taylor takes :the simple static Prisoners' Dilemma and makes it dynamic by adding the time element and allowing a number of iterations of the simple game. He terms this the Prisoners' Dilenuna Supergame. My purpose in restating Taylor's analysis here is not to reproduce his argument in all its mathematical and logical complexity, but rather 66

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to look at his conclusions based on this analysis. The "tragedy" of the commons and the "Prisoner'' status of the game players is that a rational individual making rational maximizing choices when aggregated with other rational individuals leads to Paretoinferior outcomes. This is certainly one of the basic arguments of modem state theorists for the justification of the state as a welfare maximizer. Hume, for example, argues, Two neighbors may agree to drain a meadow, which they possess in common;' because 'tis easy for them to know each others mind; and each must perceive, that the immediate consequence of his failing in his part, is the abandoning the whole project. But 'tis very difficult, and indeed impossible, that a thousand persons shou 'd agree in any such action; it being difficult for them to concert so complicated a design, and still more difficult for them to execute it; while each seeks a pretext to free himself of the trouble and expence [sic], and wou'd lay the whole burden on others. (Hume, 1888, p. 538) Taylor's of this view involves the results of his Prisoners' Dilemma Supergame a number of strategy outcomes can lead to Pareto-optimal results. There are also many strategy vectors where the Prisoner nature of the game remains, and Pareto-inferipr results are obtained. The point is that those rational, individual, I maximizing choices aggregated in the supergame can lead to Pareto-optimal results. This provides a powerful criticism to the use of such welfare maximizing difficulties in the "tragedy of commons" and "Prisoners' Dilemma" as a justification for the I necessity or imperative of the state. Even assuming a difficulty in maximizing social welfare does not,imply that the coercive state is the only or best solution. To say this, however, is only a critisim of state justifications. These results of the supergame analysis do not provide any positive rationale for the type of anarcho-syndicalist society I have presented: The moral claim of the anarcho-syndicalist vision lies in the freedom of perpetual individual revolution, of individuals who have the ability to withdraw from any association at a very low comparative opportunity cost relative to that cost when the 67

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state claims sove?egnty. That revolutionary disassociation and voluntary association could be incorporated into a system of social organization that approximates the I analogous free m:az.ket situation in economics. It is the antithesis of Wells' utopia where "[t]he welfare state governed by the samurai sees to it, as to a lesser extent do such states as exist today, that every citizen is 'properly housed, well nourished, and in good health, reasonably clean and clothed healthily"' (Wells, 1967, p. xvii). Wells' totalizing version of the welfare state into the World State sacrifices individual freedoms for rational individual and social maximized happiness. But as Doestoevski's underground man, a version of the radical individual anarchist, proclaims, a human is not a cipher. Human society c8nnot be reduced to the slope of a tangent line on a curve of maximum welfare. Society has borne the tragedy of that heart of darkness many times before. But that tangent line can be used as a basis for individual decision-making. That allows an expression of the contradiction of the rational nature of human beings who can fully recognize the meaning of that tangent line and of two plus two equals four, yet choose to put their tongue out at it This the Prospects vision attempts to do and utopian I political theory a).Iows us to contemplate. With9ut a "utopian" commibnent to question the underlying assumptions of social prnctices, proposals for reform tend to bypass .the central problems, and may ameliorate a situation which ought never to be tolerated. Secondly, as Kropotkin indicates ... there is often historical evidence that what seems "utopian" to one generation is accepted as obvious good sense by their successors. Oscar Wilde commented that "A map of the world that does not include Utopia is not worth even glancing at, for it leaves out the one country at which Humanity is always landing ... (The Soul of Man under Socialism, 43). Thiidly, as Kropotkin also emphasized, most people are prisoners of their own and of the reigning conventional wisdom. So their view shuts out large stretches of historical experience, alien areas of social reality, and a vision ot: future possibilities. (Carter, 1971, p. 83) 68

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This chapter has presented the philosophical end behind the Prospects vision. It is a I model that faces historical and logical limitations, but ones that are demonstrated to be within the range of a functional system at some minimal level with information technology as a means. The three braids of analysis of the Prospects vision, utopian political theory, information technology, and anarcho-syndicalist theory are complete. 69

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CHAPTER 6 CONCLUSION What I have tried to accomplish is not a proof that information technologies, computers, and their related intercommunication technologies, provide the technical imperative to rationally choose a democratic form of feasible, functioning anarcho.syndicalism. Rather I have attempted to demonstrate the prospects for such a system being feasible and functioning. I am no technocrat or technological pollyanna. While the central and critical proposition of this thesis is that an anarcho-syndicalist type of political system not only can be implemented using information technology as a tool to overcome limits of size and information flow, but is preferable because it expands the personal power and responsibility of the individual and the community in alienating cultures and economies, I do not believe that the experience nor research of modem society is that technological fixes, growth as the goal of an economy, nor unceasing technological innovation, will solve the problems of the human condition. I do believe that given the present set of circumstances of social life and organization as the basis for speculation of alternatives, that technologies can be used as integral tools to overcome certain physical and social limits that constrain the possibilities of creating non-coercive and non-authoritarian systems along the lines of anarcho-syndicalist theory. This leaves the question of the malleability of individuals and their psychology and the perfectibility of social life completely out of the picture, or at least at its very edges. Neither of these issues need enter into arguments concerning

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the establishment or functioning of an alternative society whose ends are desirable and whose means for achieving those ends are just, fair, and based on a radical equality. Perhaps redueed population over time, a healed environment, small-scale social, political, and economic organization, and a sustainable lifestyle would liberate human beings in greater quality and depth than any form of mass, technological society, but that is not the question, because that is not where many of the communities of the world exist, nor where most are headed. In that vein what I have discussed is not Utopia, nowhere, but rather Eutopia, a good place, one where all the problems of humanity remain, but in a dynamic and fluid flow of power, and responsibility that does not tend to magnify foibles into the forte of state, institutions, and rigid authority. It is a vision of a society where specialized administrative and complex information is readily available, where an approximated free market exists in real time and where price, supply, demand, and other microeconomic effects respond to real information in real time, and where the cost of information flow and decision-making are reduced enough to allow all who wish to participate to do so-all with the same technology. It is a vision where society and civilization are aq aggregation of the social and civil nature of individuals and the communities they chose to form and maintain, rather than a set of institutions that require the sacrifice and alienation of untold numbers of people. 71

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BIBLIOGRAPHY I Adams, R. M; (1975). Sir Thomas More, Utopia: A new translation, backgrounds, criticism. N,ew York: W. W. Norton & Company, Inc. Arrow, K. J. Social choice and individual values. (2nd ed.). New Haven: Yale University Press. Arrow, K. J. (1974). The limits of organization. New York: W. W. Norton & Company, Inc. I Benello, C. G., &. Roussopoulos, D. (Eds.). (1971). The case for participatory democracy: Some prospects for a radical society. New York: Grossman Publishers. i I Beniger, J. (1981). The control revolution: Technological and economic origins of the information society. Cambridge, MA: Harvard University Press. Bookchin, M. (1971). Post-scarcity anarchism. San Francisco: Ramparts Press. Bronowski, J. (1973). The ascent of man. Boston/Toronto: Little, Brown and Company. Carter, A. (1971).: The political theory ofanarchism. London: Routledge & Kegan Paul. I Cummings, E. E.{1980). Complete poems, 1913-1962. New York: Harcourt Brace Jovanovich.' Dolgoff, S. (Ed.).'(1974). The anarchist collectives: Workers' self-management in the Spanish revolution, 1936-1939. New York: Free Life Editions, Inc. I Erasmus, C. J. (1985). In search of the common good: Utopian experiments past and future. NewiYork: Macmillan, Inc. Hexter, J. H. (1965). More's utopia: The biography of an idea. New York: Harper and Row Inc. Horowitz, I. L. (1964). The anarchists. New York: Dell Publishing Co., Inc. Hsu, F-h., Anantharaman, T., Campbell, M., & Nowatzyk, A. (1990, October). A grandmaster chess machine, Scientific American, 263(4), 44-50.

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Hume, D. (1888): A treatise of human nature. (L.A. Selby-Bigge, Ed.). Oxford: The Clarendon Press. !nose, H., & Pierce, J. R. (1984). Information technology and civilization. New York: W.H. Freeq1an and Company. Jackson, R. (1947).The Nurnberg case, as presented by Roben H. Jackson, chief of counselforthe United States, together with other docwnents. (1st ed). New York: A. A. Knopf. Kaiser, W., Marko, H., & Witte, E. (Eds.). (1977). Two-way cable television: Experirrients with pilot projects in Nonh America, Japan, and Europe. New York: SpringerVerlag. Kelly, J. S. (1988.). Social clwice theory: An introduction. New York: SpringerVerlag. Kraemer, K. L., Danziger, J. N., & King, J. L. (1976). Information technology and urban management in the United States. The Urbis Group, Public Policy Research organization. Irvine: U'niversity of California. Mannheim, K. (1956). Ideology and utopia: An introduction, to the sociology of knowledge.i(L. Wirth and E. Shils, Trans.). New York: Harcourt, Brace and Co. Marius, R. (1985). Tlwmas More. New York: Alfred A. Knopf. Marx, K., Leriin, :V.I., & Engels, F. (1974). In Anarchism and anarclw-syndicalism: Selected writings by. New York: IntemationalPublishers. McCord, W. (1989). Voyages to utopia: From monastery to cominune-the search for the perfect in modern times. New York: W. W. Norton & Company. McLean, I. (1989). Democracy and the new technology. Cambridge: Polity Press. ' Moody, F. (1988; July/August). When work becomes an obsession. Baltimore City Paper. In lf:tne Reader. Eric Utne. (Ed.). No. 28. Nabokov, V. '(1958). Nabokov' s dozen: A collection ofthineen stories. New York: Avon Books. I Nozick, R. (1974). Anarchy, state, and utopia. New York: Basic Books, Inc. I Orwell, G. (1949).1984. New York: Harcourt Brace Jovanovich, Inc. Plant, R., Gregory, F., & Brier, A. (1988). Information technology: The public issues. Lon4on: Manchester University Press. Plattel, M.G. (19;72). Utopian and critical thinking. Duquesne Studies, Philosphical Series. Vol.;29. Pittsburgh: Duquesne University Press. 73

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,I I Proudhon, P., J. General idea of the revolution in the ninteenth century. (John Beverly Robinson, Trans.). New York: Haskell House Publishers, Ltd. (Origimil published 1923) I Rhodes, H. V. (1967). Utopia in American political thought Political theory studies. No.1. The lnstitute of Government Research. Tucson: The University of Arizona Prss. Richter, P. E. (1975). Utopia/dystopia. In Peter Finch. (Ed.). Issues in contempor4ry ethics, A Schenkman series. Cambridge, MA: Schenkman Publishing Company. Sibley, M. Q. (1971). Technology and utopian thought. In Davis B. Bobrow, & Samuel Krislov (Eds.). A series on critical issues in political science. Minneapolis: Burgess Publishing Company. Skinner, B. F. (1948). Walden two. New York: Macmillian Publishing Co., Inc. Sugden, R. (1981). The political economy of public choice: An introduction to welfare economics. New York: John Wiley & Sons. Taylor, M. (1976). Anarchy & cooperation. London: John Wiley & Sons. I Taylor, M. Community, anarchy & liberty. London: Cambridge University Press. I Teliranian, M. (1990). Technologies of power: Information machines and democratic prospects. New Jersey: Ablex Publishing Company. Teich, A. H. (1990). Technology and the future. (5th ed.). New York: St. Martin's Ventura, M. July/August). Someone is stealing youdife. LA Weekly. In Utne Reader. Eiic Utne. (Ed.). No. 46. I Walters, K. (1989). The sane society ideal in modem utopianism. In Problems in contemporary philosophy. Vol. 7. Lewiston: The Edwin Mellen Press. Wells, H. G. A modern utopia. Lincoln: University of Nebraska Press. Westin, A. F. (Ed.). (1971) Information technology in a democracy. In Harvard studies in technology and society. Cambridge, MA: Harvard University Press. Zorkoczy, P. (1984)./nformation technology. New York: Van Nostrand Reinhold Co. Zwerdling, D. (1984). Workplace democracy: A guide to workplace ownership, participation, and self-management experiments in the United States and Europe. New York: Harper and Row, Publishers, Inc. 74

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Adams27 }UTow49, 50,51,52,53,55,56 Bacon 37,48 Bakunin56. Becker46 Bellamy? Beniger3 Bookchin 63 Borda 50 Bronowski 1, 28 cable 42, 43 Campbell46 Carter35, 68 Catlin 32 CATV43 Chadwick46 Condorcet 50 decision-making.4, 5, 23, 31, 35, 40, 44, 58, 60,' 62, 68, 71 Doestoevski 68 Dolgoff60 Engels 28, 61 Eutopia 71 Freud29 Galton 50 Goodman47 Goodwin 6 Green movement Hardin65 Heinrich-Hertz-Institute 43 lllii 43 Heisenburg' s uncertainty principle 48 Hobbes 35, 55, 59 Horowitz 6, 7, 60, 61, 62 Hume67 Institutional Possibilities Frontier 41 IPF 41, 48 Kaiser43 Kelly 49, 50 Kropotkin 68 Laplace 50 Luce65 Lynd32 Mannheim 31, 45, INDEX 75 Marius 2 More2, 7 Utopia 2, 27 Nabokov 1 Nanson 50 Nozick 33 Orwell7, 38 dystopian 33 Ovid7 Pelloutier 61 Plato7 Plattel28 Production Possibilities Frontier 41 PPF41 Proudhon vii, 6, 33, 64 Qube42 Raiffa65 Rawls 6, 52, 54 Rhodes 32 Utopia 32. Ricardo 55 Sarvodaya movement 4 Shelley 38 Sibley 37, 38 Skinner 31 Slaton46 Smith 55 social choice theory 5, 49 Sorel 56 Sugden 51, 52 Taylor 58, 59, 66, 67 Tehranian 4, 38, 42, 45, 46, 47, 48 Teich 3, 47 tele-education 43 teleshopping 42 Televote 46, 47 televoting 46,47 Trade unionism 6, 60 Walters 30 Wells.68 Utopia 68 Westin44 Wright37



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REACTIONS OF SUBSTITUTED BIBENZYLS AND a'-HYDROXYBIBENZYLS WITH SUPERCRITICAL WATER UNDER COAL LIQUIFACTION CONDITIONS by Akiko Horiuchi B.A., International Christian University, 1969 A thesis submitted to the Faculty of the Graduate School of the University of Colorado in partial fulfillment of the requirements for the degree of Master of Science 1988

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This thesis for the Master of Science degree by Akiko Kusuoka Horiuchi has been approved for the Department .of Chemistry by Anderson Date .:L-(, I ?d'JY

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Horiuchi, Akiko (M.S., Chemistry) Reactions of Substituted Bibenzyls and a'Hydoxybibenzyls with Supercritical Water under Liquifaction Conditions iii Thesis directed by Assistant Professor Michael A. Mikita Supercritical fluids have attracted special interest due to their unique physical properties which do not exist under common laboratory conditions. Recently, supercritical water has been studied as a coal liquifaction medium due to the relatively high coal conversions exhibited in supercritical water and its economic advantages. The object of this thesis was to examine the role of water under coal liquifaction conditions using substituted bibenzyls as the coal models. To accomplish this goal, series of substituted bibenzyls and a'-hydroxybibenzyls were synthesized via Wittig reaction with subsequent hydrogenation. The substituents synthesized were p-NH2 p-t-Bu, p-CH3 H, m-CF3 and p-CH3o2c. Both sets of compounds were reacted in a multi reactor system containing water under 4290 psi (0.30 kbar) at 400C for 3 hours corresponding to a supercritical water density of 0.095 g/mL. In many instances deuterium oxide was substituted for water. The

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iv dichloromethane soluble extracts from these reactions were analyzed via gas chromatography-mass spectrometry. Thermolysis pathways dominated the observed products from the substituted bibenzyls. Both the thermolysis products and recovered starting materials were observed to undergo deuter.ium exchange. The observation of exchange implies previously unknown reaction pathways water and bibenzyls under liquifaction The mechanisms for these reactions were not rigorously established, although electon donating substituents favored substitution suggesting an ionic pathway. In the case of p-carboxylic acid methyl ester bibenzyl, demethylation and decarboxylation predominated with a deuterium substitution pattern suggestive of an ionic pathway. Comparison of the product distributions in H 2o and o2o for the a'-hydroxy substituted bibenzyls suggests a primary isotope effect. This is an intriguing observation considering that the thermolysis pathway predominated. The a'-hydroxybibenzyls exhibited more extensive deuterium exchange than the simple bibenzyls, presumably due to the enhanced H(D)-atom transfer ability of the phenolic-H(D). The tautomerization pathway contributed

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v significantly to the product distribution with the a' hydroxybibenzyls. They also exhibited a primary isotope effect suggesting that the tautomerization is rate limiting. 2-Ethyl-4-substituted biphenyl ethers were also observed in some cases, presumably through the rear rangement of certain substitued a'-hydroxybibenzyls. Cyclization of p-NH2 p-CH3 and H a'-hydroxy substituted bibenzyls to dibenzodihydrooxepane was also observed.

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Like all other arts, the of Deduction and Analysis is one which can only be acquired by long and patient study, nor is life long enough to allow any mortal to attain the highest possible perfection in it. Sherlock Holmes, in "A Study in Scarlet"

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To Katsura, Shu, Hokuto, and Tadashi.

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ACKNOWLEDGEMENTS I would like to express my greatful thanks to my mentor Dr. Michael A. Mikita, for his instructions, encouragements, and ever lasting zest for chemistry. To Seifu Tadesse, Joel Boymel, Bonnie O'Connell, Roger Simon, for teaching around the lab and keeping the spirits up. To Dr. Robert Meglen and Dr. Larry Anderson for careful reading of the draft and helpful suggestions. To Tadashi without whom my entire research would have being impossible. I also like to express my gratitude to Prof. Paul Fenessey and Mr. Alan Quick, of Univ. of Colorado Health Science Center for MS analysis. To Dr. Bradley Brockrath of US Dept. of Energy, Pittburgh Energy Tech nology Center, for encouragement and support. and to Mr. Henry Davis for running the multireactor system. To Oak Ridge Associated Universities for their financial assistance in travel to Pittburgh by MAM. Finally, financial support by US Dept. of Energy (DE-FG22-85PC81544) is also greatly acknowledged.

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CONTENTS CHAPTER I. INTRODUCTION ...... 1-1 Object of the Study .... 10 II. SYNTHESIS OF SUBSTITUTED BIBENZYLS 12 2-1 Selection of Wittig Reagent 19 2-2 Protection of Hydroxy Group . 20 2-2-1 Acetyi ether .. 21 2-2-2 2-Tetrahydropyranyl ether . 21 2-2-3 Benzyl ether 22 2-3 Attempts to Synthesi e p-Bromobibenzyl ... 22 2-4 Attempts to Synthesi e p-Nitrobibenzyl 23 2-4-1 Reduction of p-nitrostilbene via hydroboration... 23. 2-4-2 Reduction of p-nitrostilbene via diamide .............................. 23 2-4-3 Hydrogenation of p-nitrostilbene using rhodium as a catalyst 26 2-4-4 Oxidation of p-aminobibenzyl with peroxytrifluoroacetic acid 26 2-4-5 Grignard reaction with copper iodide catalyst. 27

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X III. RESULTS AND DISCUSSION 28 3-1 Substituted Bibenzyls where R H 32 3-2 Substituted Bibenzyls where R OH 42 3-'3 Future P 1 ans ..... 49 3-4 Conclusions 49 IV. EXPERIMENTAL. 52 4-1 Synthesis . 53 4-1-1 a-Bromo-p-toluic acid methyl ester 53 4-.1-2 Salicylaldehyde benzyl ether 53 4-1-3 Salicylaldehyde acetyl ether 54 4-1-4 Salicylaldehyde tetrahydropyranyl ether. . . . . . . . . . . . . . 5l.J 4-1-5 Pyridinium-p-toluenesulfonate 55 4_-1-6 Diethyl-p-methylbenzylphosphate 55 4-1-7 4-Methylstilbene 56 4-1.-8 4-Methylbipenzyl 56 4-1-9 p-Bromobibenzyl ....................... 57 4-1-10 p-Nitrobibenzyl 57 A) By hydroboration reduction 57 B) By diimide reduction 58 C) By nydrogenation with rhodium catalyst 58 D) By oxidation with peroxide 59 E) By cuperous iodide coupling 59

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xi 4-2 Reactions .... 60 REFERENCES 64 APPENDIX ..................... 68

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xii TABLES TABLE 1. Product Analysis of Thermolysis of Bibenzyl by Various Researchers . 9 2. Compounds used in the Reaction .. 15 3. Preparation of Phos phonates 16 4. Preparation of Substituted Stilbenes . 17 5. Preparation of Substituted Bibenzyls 18 6. Reaction of p-Nitrostilbene with Borane Complex 24 7. Reaction of p-Nitrostiblene with p-Toluene-sulfonhydrazide 25 8. Hammett of Groups Used in the Reaction................................... 31 9. Product Distributions of Major Products 34 10. Summaries of the Reactions . 63

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FIGURES FIGURE 1. Ionization constant of water in high-temperature fluids of various densities .................................. 3 2a. Hydrocarbon solubility (w%) in water .. 3 2b. Inorganic solubility (w%) in water 3 Xiii

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CHAPTER I INTRODUCTION The ability of supercritical fluids (SCF) to dissolve inorganic salts was first reported by Hannay and Hogan at a meeting of the Royal Society of London in 1879. 1 It was only during this past decade, however, that the principles and practice of supercritical fluids have experienced rapid advances. Supercritical fluids have been applied to areas such as polymer and monomer processing, natural product and pharmaceutical process-ing, treatment of waste and coal liquifaction. Motivation for the development of supercritical fluid technology is a result of the high costs for energy-intensive separation techniques such as distillation. Increased environmental awareness has also intensified the search for non-toxic fluids to refrain traditional industrial solvents, such as chlorinated hydrocarbons. Increased demand for process techniques which tradi-2 tional methods cannot meet and increased interest in reactions under high temperature and/or pressure from a pure chemistry point of view have together hastened research with SCF.

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2 The possible use of supercritical fluids in coal liquifaction has recently attracted significant inter-est. The typical solvent for coal liquifaction is an organic solvent which can act as hydrogen donor, such as tetralin. These donor solvents are commonly hydrogena-tion products of coal liquifaction and thus refered to as process derived solvents. The disadvantages with the use of these solvents are high cost of their separation from other products, and the necessity of subsequent hydrogenation to make more efficient hydrogen donating species. Some donor solvents also become fixed. in the insoluble residue following liquifaction. Among common solvents, water has attracted special interest because of its low cost and relatively high coal conversion rate.3 Water has a critical temperature of and critical pressure of 217.7 atm. Above this critical temperature, a liquid phase does not exist regardless of the pressure. Consequently, supercritical water can be more liquid-like or more gas-like depending on density. Thus water above its critical temperature is most commonly referred to as a fluid. The ionization constants of water in high temperature fluids of various densities 4 is expressed in Fig. 1 For example, when density is doubled at 400C the ionization constant increases by

PAGE 16

3 -8 -9 , c:: Density= 0.7 IG -10 , "' c:: 0.6 , 0 , u -11 c:: 0.5 0 , .... , \ IG N -12 "( o.'4 .... c:: , 0 ,, ,,. .... , \4-13 ,,, 0 0.3 0'1 I 0 ...J -14 I o' 0 200 400 600 Temperature, oc Fig. 1. Ionization constant of water in high-temperature fluids of various densities. The solid line is the experimentally determined curve for liquid water under its own vapor pressure. The estimated extrapolation of the curve to the critical point is shown as a dashed line. The other dashed lines shown calculated values of the constant for single-phase fluid water under sufficient pressure to maintain the indicated densities. 3: 50 J ....... -300 400 Fig. 2a. Hydrocarbon solubility (wt %) in water :lOOt 3: 50 ...__...._1 __ ,.__ 300 400 Fig. 2b. Inorganic solubility (wt %) in water

PAGE 17

about three powers of ten. Temperature and pressure dependence of dielectric constant allow convenient control of solvent properties over a large range. The ionization constant of liquid water increases with temperature, then drops rapidly just prior to the criti-cal temperature. As the result, the solubility of hydrocarbons in water increases dramatically as it reaches supercritical temperature(Fig. 2a, Fig. 2b).ij Wender, et al.,(198ij) have shown that when coal is treated with supercritcal water alone, the amount of THF extractable products depends upon the water density. 5 Barton (1983) has indicated that, in coal liquifaction, water is a good extraction solvent as well as good transportation medium. 6 Stenberg and co-workers (198ij) studied supercritical water in presence of hydrogen sulfide. Under their conditions, water acted only as slurry liquid and did not participate in reactions.ij In addition to the physical roles, water may participate as a reactant. In combination with carbon monoxide and hydroxide as catalyst, Ross and co-workers found that water first reacts with carbon monoxide to form formate which in turn reacts as a reducing reagent. In this case, water is a hydrogen source.7 8 In contrast to the carbon monoxide -water system, in the hydrogen sulfide -water system studied by Stenberg, hydrogen

PAGE 18

5 sulfide acted as hydrogen donor while water did not 4 react. In the thermolytic reaction of bibenzyl ether in water, Paulaitis, et al.,(1983) have shown that bibenzyl ether decomposed at 400C by both pyrolytic and hydrolytic pathways, later leading to the formation of benzyl alcohol, indicating direct participation by water.9 Recent experiments in this laboratory did not exhibit an isotope effect when coal was liquified with H 2o or c2o along with tetralin and hydrogen. These suggest that under the experimental conditions, water was not a rate limiting reactant. Similar experi-ments in the absence of molecular hydrogen suggest that molecular hydrogen plays dominant role regardless of mechanism.10 Our group also has shown that when 4benzyl phenol was reacted with c2o, recovered 4-benzyl phenol contained at least two deuteriums. One explanation for this observation may be electrophilic aromatic substitution of deuterium.11 The reaction of hydroquinone monobenzylether in c2o resulted in the formation of triply-deuterated catechol monobenzyl ether. While the formation mechanism is still uncertain, this is another indication of possible ionic pathways in the reaction of 12 supercritical water.

PAGE 19

6 Based upon this overview, it appears that super-critical water sometimes plays a physical role, and sometimes acts as an active participant. If the water is a reactant, how does it react? If it behaves as a sol-vent, does it assist reactions? These are some of the many questions that still need to be answered regarding coal liquifaction in a super critical water system. The behavior of bibenzyl at high temperature has been studied intensively by previous researchers. In 1979, Virk proposed a concerted mechanism in which the intermediate (VI) takes hydrogen from dihydronaphthalenei followed by the cleavage of phenyl-phenyl bond. 13 (VI ) This mechanism was immediately rejected by others. Stein and Miller (1979) calculated the rate of reaction based on the proposed mechanism and pointed out that the observed k=105sec-1 was too slow for the calculated value of k=10-12 6 sec-1 14 Vernon (1979) also indicated that thermolysis of bibenzyl is not accelerated by the presence of tetralin, a good hydrogen donor, indicating 15 no proton transfer. Stein's and Vernon's results

PAGE 20

7 supported a radical mechanism where radical cleavage of ethane bond is proposed to be the rate determining 16-19 step. The thermolysis radical cleavage mechanism of bibenzyl is illustrated in Scheme 1. Scheme 1 L @CH3 + @-CH=ca-@ Extensive kinetic studies of pyrolysis of biben-zyl in liquid phase at 300C-425C was done by Miller and Stein (1981).20 The results where all in agreement with a radical mechanism were the production of toluene is first order in bibenzyl. Livingston, Zeldes and Conradi (1979) observed 1,2-diphenylethyl radical by ESR

PAGE 21

8 when bibenzyl was heated to 460C-560C. In the presence of excess toluene, benzyl radical was observed at 560C.21 Ross and Blessing (1980) calculated half life-times of bibenzyl at 400C and 335C, and found t 112 to be 2.0 hrs and 160 hrs respectively,22 based on log k -1 23 (sec ) = 14.4-57/2.303RT. They concluded that under the standard reaction time of 30 min, thermal scission can not play a significant role at these temperatures. They also noted that coal conversion rate is not directly related to the hydrogen donating ability of the solvent, raising a question on the previously accepted mechanism of simple thermal cleavage followed by capping with proton. Vernon (1980) studied hydr6cracking of bibenzyl at 450C, 30 min, in the presence of tetralin, tetralin and molecular hydrogen, and molecular hydrogen alone. Conversion rate increased when molecular hydrogen was added to the tetralin. Also, conversion rate increased as hydrogen pressure increased. This indicated direct 24 participation of molecular hydrogen. The product analysis of the thermolysis of bibenzyl at various temperatures, pressures and reaction times, has been studied by Poutsma (1980).25 The products of reactions, done by various researchers has

PAGE 22

Table 1 Product Analysis of Thermolysis of Bibenzyl by Various Researchers Product distribution (carbon Researchers Tamp. Time p Conv.l Conditions 12lCH3 .0CH=CHm tli2CHCH3 (JZ1CH2CHtll )2 (JZICH2)2CHIZJ IZICH2CH3 Phenonthrene tli2CH2 IZl Poulmt (1) 4o1"c 1' mill '4 Kf't 1.7 oOIT\busuon tubt 26.7 9.7 1.1 3,.2 26.7 -d d 0.6 401 20,., 52 ne lo,d1otlfon of ohakn1 ,4.7 32.6 0.6 0.6 ,_, ,,4 1.7 1.6 401 15 mill 1tqutd 1.4 30.0 10.6 11.2 44.6 3.3 d d 0.3 401 20,., 1tqutd 85.0 58.8 7.3 3.4 2.2 1.0 -2.4 18.3 t .0 ( 2 ) 400 2hr 1tqutd 71.2 2-11 rnrn 38.1 n.4 t:u 8.0 2.8 0.8 1.9 2.6 400 30 mtn Hqutd 4.9-6.0 lubo, no shakfn1 11.0.7 12.4 12.4 31.2 5.4 f.S 2.9 2.0 Yomon(l) "":J 30 mtn 1tqutd 69,1 1.!orn 11 20 om Mo 411.7 41.& . 0.3 1.0 s.o 1.2 1ood: o.s-t .o 1 otow agtlolten (mo10J) 11 (earbon no.)/14 (I) H.LPoulsmt, Fuo1 1980,59, US. (2) L.H.Vtr11011, Fuo1 1980, 58, 102. (3) R.E.Hm.r, s..stot., J. f'bol. c:Mtn. 198!, as, sao. \.0

PAGE 23

10 been summarized in Table 1. While toluene and stilbene were common products, the reactions of bibenzyl at high temperatures is temperature sensitive as well as reac-tion time sensitive. Kakemura, et al., (1981) found that bibenzyl in a carbon monoxide/water system with cobalt or molybdenum as a catalyst, forms di-and tri-methylated benzenes along with other minor products. Benzene and toluene were the major products.26 In the presence of metal catalysts the reactions seem to take completely different pathways. 1-1 Object of the Study At first glance, water would appear to be neither a good solvent nor a good reactant. for the commonly employed coal liquifaction model reactions. The object of this thesis was to study the behavior of supercritical water in presence of a series of coal models to examine whether water exhibits solvent properties or reaction chemistry under liquifaction conditions. Substituted bibenzyls were chosen as the coal model compounds for two basic reasons. First, bibenzyl is the most studied of the coal model compounds at high temperatures, consequently it provides the most

PAGE 24

11 established mechanistic pathways. Secondly, unlike benzyl ethers which when radically cleaved will exhibit some ionic character to the transition states, bibenzyls are not expected to exhibit significant ionic character. Consequently, ambiguity between radical reactions and ionic reactions will be minimized.

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CHAPTER II SYNTHESIS OF SUBSTITUTED BIBENZYLS All the bibenzyls used in the reaction with supercritical water were synthesized according to the reactions illustrated in Scheme 2 to 4. Phosphonates (Ia -Ig) were synthesized from substituted benzyl halides and triethylphosphite (Scheme 2). All substituted benzyl halides were commercially available except a-bromo-p-toluic acetate which was synthesized from the methylation of a-bromo-p-toluic acid with diazomethane.27 Scheme 2 Synthesis of Phosphonates R 1-CHi 2r. -CH2-(Q( X 0 v R1 = Br or Cl )( v ,. N02 H lb t-Bu H lc CH3 H ld H H ,. H CF3 ., f CH30CO H lg Br H

PAGE 26

1 3 The phosphonates were coupled with benzaldehyde or protected salicylaldehyde, via Wittig reaction to form the stilbenes (Scheme 3). Scheme 3 Synthesis of Stilbenes R2 X v )( v R2 )( 11411 N02 H H 111411 N02 II b t-Bu H H lllb t-Bu lie CH3 H H lllc CH3 II d H H H llld H II H CF3 H Ill H II f CH30CO H H lllf CH30CO llg Br H H lllg Br Salicylaldehyde was protected as the benzyl ether, according to the reaction illustrated below. (Qt COH OH (Q( COH OCH2@ Finally, the stilbenes were hydrogenated to v H H H H CF3 H H obtain the bibenzyls (IVa-IVf, Va-Vf), (Scheme 4). R2 0CH20 0CH20 0CH20 0CH20 0CH20 0CH20 0CH20

PAGE 27

14 Sheme 4 Synthesis of Bibenzyls H2 /Pd ) X v R3 X v R3 IVa NH2 H H Va NH2 H OH IVb t-Bu H H Vb t-Bu H OH IVc CH3 H H Vc CH3 H OH IVd H H H Vd H H OH IVe H CF3 H Ve H CF3 OH IVf CH30CO H H Vf CH30CO H OH All substituted groups were unaffected by hydrogenation, except benzyloxy, bromo and nitro groups. Benzyloxy and bromo groups were eliminated while the nitro group was reduced to the amino group. The physical properties of these substituted bibenzyls are complied in Table 2. The synthetic results are summarized in Table 3 -5. A more detailed discussion of each of these synthetic steps will now follow.

PAGE 28

R Table 2 Compounds Used in the Reaction v R X v Compound m .pt. e>ep/lit c m .wt. m/e [relative sensltfvity] H NH2 H IVa 42-44/48(1 ) 197 197(25, M+], 1 06( 100, M+] H t-Bu H IVb 37-38/ 238 238(25, 147[ 100, M+-PhCH2 ] H CH3 H IVc 25-26/24-26 (2 ) 196 196[25, M+], 105[100, M+-PhCHz) H H H IVd 48.5-49.5/52-52. 5 (3 ) 182 182(49, M+], 91[ I 00, M+ -PhCHz ] H H CF3 IVe lfquid 250 250(25, M+], 159[ 18, M+-PhCH2 ], 91[ 100, PhCH2J H CH30CO H IVf 28-29/ 240 240[25, M+], 149(20, M+-PhCH2 ], 91( 100, PhCHz) OH NH2 H Ve 138-144/ 213 213[ 14, M+], 1 06(1 00, 1-1'1 -HOPhCHz ] OH t-Bu H Vb 58-59.5/ 254 254[42, M+], 147[ 100, M+HOPhCH2 ) OH CH3 H Vc 54-55/ 212 21 2[42, M+], 1 07(1 00, M+Cli 3PhCHz ], 1 05[1 00, OH H H Vd 79-80/85 (4 ) 198 198[27, M+], 1 07(1 DO, M+-PhCHz pM+-HOPhCHz J OH H CF3 Ve 43-44.5 I 266 266[25, M+], 109[100, M+-cF3PhCH2 ] OH CH3oco H Vf 92-100/ 256 256(14, M+], 107(100, M+-cH30COPhCH2 ] ..... lJ1 (1) .J V Braun, H.Dutsch, O.Koscilski, Br.1913, 46,1511. (2) R.L.HinHan, K.L.Hamm, J.Am.Chm.Soe. 1959,81,3294. (3) Hrck lndx (4) P .Ruggli, A Staub, Hlv Chirn.Acta. 1931, 20, 31.

PAGE 29

Table 3 Preparation of Phosphonates R 1-CH2-
PAGE 30

Table 4 Preparation of Substituted Stilbenes R2 (Eto>2r, -cni-Cll = Cll -@ 0 v R2 v --mmole R2 mmole reoct prod gm/mmole % m.pt."c comp gm gm lime yield yield eKp/Jil oppeoronce 5.00 20.7 H 2.20 20.7 3 hrs 2.54/12.8 61.6 149-150/156 11 powder lb 3.68 22.5 H 2.3, 22.5 3 lib 2.12/6.3 28.4 ,5.5-,7/ w noodle lc 3.62 15.0 H 1.60 15.0 48 lie 2.08/10.7 71.5 117-118/110-2 11 plat I d 3.42 15.0 H 1.60 15.0 48 lid '2.30/12.8 85.2 122-123/124 w plat It 3.10 10.4 H 1.11 10.4 8 II 1.7917.2 69.4 58-S9 I w noodl If 1.72 6.0 H 0.64 6.0 3 11r 0.4Sll 31.0 ISO-lSI I wplat. I 9 5.06 16.0 H 1.70 16.0 2 119 3.60/13.9 86.8 136-137/139 w nePdlo 1.84 7.7 .0CH20 1.62 7.7 3 Ill I.Sa/4.78 62.S 102-103/101 11 nudle I b 2.84 10.0 .0CH20 2.12 10.0 a Ill b 1.51/4.42 44.0 68.S-6'/ w plate I c 3.24 13.4 .0c112o 2.84 13.4 8 lllc 1.98/S.OS 37.7 58-59/ v needle I d 4.00 17.5 .0CllzO 3.71 17.5 8 llld 2.60/9.0' 51.9 65-66 I 11 plat It 5.00 16., .0c11 2 o 3.S8 16.9 a Ill 4.39/12.4 73.3 II oil If 4.58 16.0 .0CH20 3.39 16.0 3 mr 1.00/2.9 I 8.1 11 oil 19 3.31 10.7 .0CH20 2.27 10.7 2 Ill 9 1.85/5.07 47.4 66.5-67.0/ w povdor

PAGE 31

Table 5 Preparation of Substituted Bibenzyls Reactants Solvent Pd React Product comp gm mmole type ml gm t1me comp gm mmole yield II a 2.70 12.0 EtOHITHF 100/100 0.20 2hrs IVa 2.35 11.9 99.4 lib 1.83 7.61 EtOH 200 0.10 2 IVb 1.80 7.55 99.3 lie 1.87 9.52 EtOH 200 0.10 2 IV c 1.62 8.31 87.3 lid 1.50 8.30 EtOH 200 0.10 2 IVd 1.39 7.64 92.0 II 2.41 9.71 EtOH 220 0.12 2 IV 2.40 9.66 99.4 llf 0.45 1.88 EtOHITHF 180/20 0.10 2 IVf 0.44 1.83 97.5 llg 1.45 5.59 EtOH 200 0.10 2 IV d 0.95 5.20 93.0 lila 2.46 7.43 EtOH/THF: 200/50 0.30 4 Va 1.50 7.14 94.7 lllb 1.27 3.70 EtOH 200 0.20 2 Vb 0.97 3.82 103 lllc 0.95 3.70 EtOH 200 0.20 2 Vc 0 .64 3.02 94.9 ,_. (X) llld 1.28 4.46 EtOH 200 0.30 2 Vd 0.97 4.91 110 Ill 4.39 12.4 EtOH 200 0.50 2 v. 3.60 13.5 109 lllf 1.00 2.90 EtOHITHF 150/50 0.30 3 Vf 0.98 2.82 97.3

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19 2-1 Selection of Wittig Reagent Two types of Wittig reagents 'were considered. Triphenylphosphite, which, after reaction with. benzyl halide followed by base, forms the phosphorus ylide that reacts as the nucleophile. The other was triethylphos-phite, which reacts with benzyl halide to form diethyl-phosphonic benzyl ether followed by treatment with base, generating phosphonate carbanion, another strong nucleophilic specie. After isolation of triphenylbenzylphosphonium bromide and diethylphenylphosphonate, both compounds 28 29 were reacted with benzaldehyde. Both produced stilbene but reaction with diethylphosphonate exhibited fewer side products, as identified by TLC. There are three other advantages to the use of diethylphenylphosphonate. The first is the nucleophilicity of the intermediates. Phosphonate car-banions are known to be more nucleophilic than analogous ylides.30 The second is the required reaction condi-tions. In the reaction of phosphonium bromide, n-butyl lithium, a pyrophoric and a highly moisture sensitive liquid, is used as a base. Consequently, extreme care must be taken in its handling, and the reaction must be done under a dry, inert atmosphere. On the other hand,

PAGE 33

20 the reaction with phosphonate requires only sodium hydride as a base. The latter reaction requires simply the use of a drying tube rather than the dry, inert atmosphere. The third advantage is the physical form of the synthetic intermediates. The phosphonates are usually liquids, whereas the phosphonium bromides are solids. Solids are often difficult to obtain from oil. As a result, phosphonate was selected as Wittig reagent. 2-2 Protection of Hydroxy Group In the syntheses of a'-hydroxybibenzyls, salicylaldehyde was used as a synthetic precursor. In these syntheses, the hydroxy group must be protected prior to Wittig reaction. The requirements for the selection of good hydroxyl protecting groups are: 1) they must react quantitatively with the hydroxyl group, 2) they should not interfere with the main reaction, 3) they must be eliminated easily to return the original hydroxyl group.

PAGE 34

21 2-2-1 Acetyl ether The acetyl group was first chosen as a protecting group since it is one of the most common protecting groups, with simple synthetic procedures, and can be eliminated readily under mild conditions. Salicylaldehyde acetate was synthesized, following the standard method.31 Salicylaldehyde acetate was reacted with diethylbenzylphosphonate. The IR spectrum of the dark yellow oil thus obtained revealed hydrogen bonded OH, indicating the loss of an acetyl group. Consequently, this method was abandoned. 2-2-2 2-Tetrahydropyranyl (THP) ether THP ether was selected next since, in our laboratory, protection of salicylic acid was success-fully accomplished by THP. Preparation of THP ether was carried out following Miyashita's method,32 in which pyridinium-p-toluenesulfonate (PTS)3334 is used as a catalyst. Most of the starting materials were still unreacted after 4 hrs, 24 hrs, and 48 hrs. Consequently, this method was also abandoned.

PAGE 35

22 2-2-3 Benzyl ether In a benzyl ether, the bulky phenyl group is separated by one methylene group which would be expected to reduce steric hinderance. Benzyl ether is particulary desirable since it can be eliminated by hydrogenation, simultaneous with the reduction of the double bond in the stilbene. The benzyl ester of salicylaldehyde was synthesized in relatively good yield (60 %) by Miyano's method.35 The subsequent Wittig reaction was also successful. The benzyl group was quantitatively eliminated during hydrogenation in the presence of excess palladium catalyst. Thus all a'-hydroxybibenzyls were synthesized using salicylaldehyde benzyl ester via a'benzoylstilbenes. 2-3 Attempts to Synthesize p-Bromobibenzyl Since hydrogenation of p-bromostilbene (Ilg) resulted in elimination of bromide, direct bromination of bibenzyl with bromine and a catalytic amount of iron, was attempted following Litz.36 Four experiments were done varying reaction time temperature and ratio of the starting materials. GC/MS analysis indicated seven major

PAGE 36

23 products, including p-bromobibenzyl, p-bromostilbene (IIg) and dibromo compounds. Since the.capillary column GC retention times were very close to each other, separation of the products was not attempted. 2-4 Attempts to Synthesize p-Nitrobibenzyl Hydrogenation of p-nitrostilbene (IIa) resulted in reduction of the nitro group to the amino group. Several attempts were made to synthesize and separate pnitrobibenzyl using alternative methods. 2-4-1 Reduction of p-nitrostilbene via hydroboration p-Nitrostilbene (IIa) was treated with borane-pyridine and borane-THF complexes, varying solvent, temperature, reaction time and ratio of the reactants,3738 as shown in Table 6. Run B resulted in the best p-nitrobibenzyl/(IIa) ratio (0.56). Separation was not attempted. 2-4-2 Reduction of p-nitrostilbene with diamide p-Nitrostilbene (IIa) was reacted with ptoluenesulfonhydrazide, a diamide precursor, following Dervey and Tamalen's method.39 Reaction conditions are

PAGE 37

Table 6 24 Reaction of of p-Nitrostilbene with Borane Complexes H3B:Py H3B:THF Run I Ia* B* A* Solvent Reaction Conditions NBB/IIa** to INke nF II + B : refluK 2 hr I over nfght NP Hidio + A : to make solution cfdil: 2 eKcess hetto 60C NP 3 lla + B : hr t room tl!mp NP followed by rtfulKing at 60 C 4 1/3 Mtsityltne II + 8 : 80 c I 30 min 0.032 + A : rtflUIC over night 5 Trig 'Iyme IIi + 8 : 21 0 c I 30min 0.36 +A: 21oc, 90mln 6 excess Trig 'Iyme II+B :21oc, 30mtn 0.37 +A: 210 c, 90 min 7 Trig 'Iyme lla : 130 c +a :21o c, detect. 30 min,+ A: 8 Triglyme lla+B:21oc, 1 hr 0.56 +A: 21oc, 30min 9 1/3 Triglyme lla+8 :21oc, 30min NP +A: 21oc, over night 10 lli+B :-2c, bringtor.t. NP +A:6oc, 1 hr 11 1/2 Trig 'Iyme IIi + B : -2 C 1 hr, bring to NP r.t., +A: 21oc, 30min 12 II + B : -7c bring to r.t. NR sft over night, + A : !f! in mol ratios of lla : B : A !f! !f! ratios of puk areas obtaind and idntifid by GC/MS 1 quipd with thrmal ionization dtctor. B : bor an-comp lxs 1 A : propionic
PAGE 38

25 Table 7 Reaction of p-Nitrostilbene with p-Toluenesulfonhydrazide Rul"' 2 3 !f. iii II a TSH sol vent 2.3 triglyme 2.3 DME 2.3 triglym II! in mo 1 ratio. react. condi t 1 ons 170 c, 1 Omin 135 c, 30 min KOH,s min 70C, 35 min no. of GC peaks 24 28 4 11 PNBB/IIa 1.73 0.72 0.21 0.11 :t: iii ratio ofp.
PAGE 39

26 summarized in Table 7. The best p-nitrobibenzyl/(IIa) ratio (1 .72) was obtained in Run 1, however there were large amounts of products and the quantitative separation was not attempted. Hydrogenation of p-nitrostilbene using rhodium as a catalyst Since rhodium is known to be a selective hydrogenation hydrogenation of (IIa) was attempted using rhodium on aluminum as a catalyst. The products included p-nitrobibenzyl, (IVa) and starting material. The ratio of p-nitrobibenzyl/(IVa) was Separation was not attempted. Oxidation of p-aminobibenzyl with peroxytrir1uoroacetic acid Peroxytrifluoroacetic acid is known to be a suitable oxidation reagent for aromatic amines. p-Aminobibenzyl (IVa) was oxidized with peroxytrifluoroacetic acid, following Pagano and Emmons' method. There were four products, including p-nitrobibenzyl and (IVa). The of pnitrobibenzyl/(IVa) was 1.12. Although this method seemed to be promising, the use of 90 % hydrogenperoxide to generate peroxytrifluoroacetic acid, discouraged us

PAGE 40

27 from running the reaction on a preparative scale. Grignard reaction with copper iodide catalyst It is known that copper(I)-catalyzed reaction of Grignard reagents and organo halides result in the cross-coupling reaction of different organic Benzyl magnesium chloride and p-nitrobenzyl bromide were reacted in the presence of copper iodide. pNitrobibenzyl was obtained along with bibenzyl and two other side products. The ratio of pnitrobibenzyl/bibenzyl was 0.26. Although the yield of p-nitrobibenzyl/bibenzyl was not appreciable, the separation using preparatory TLC was attempted. Although four distinctive spots were clearly separated on the small scale silica gel TLC plates with benzene as developing solvent, preparatory silica gel TLC exhibited twenty seven visual bands. Each major band was analyzed by GC/MS with only one fraction containing the desired product in insufficient yield.

PAGE 41

CHAPTER III RESULTS AND DISCUSSION 4 Based upon the conclusions of Stenberg, water would be expected as a reactant only if the reaction of the substituted bibenzyls are ionic. An ionic alterna-tive exists to the radical thermolysis pathway if quinone methides are from a'-hydroxy substituted bibenzyls.43 This is illustrated in Scheme 5. Scheme 5 x-@-7 x-@CH2 D + DO no exchange

PAGE 42

29 The quinone methides could subsequently react with water to form hydroxy cresols, a species which would not be expected from radical reactions. The reaction of both sets of models with deuterium oxide was expected to be most informative. The incorporation of deuterium into products from the sub-stituted bibenzyls would strongly suggest ionic reac-tions. The homolitic bond strength of H-OH in water is 119 kcal/mole, significantly higher than C-H bond (98 kcal/mole) or c-c bond in bibenzyl (61.6 kcal/mole)(Appendix 1). Consequently, in radical reac-tions water would not be expected to react sig-nificantly. This was the crux of Stenberg's explanation of his experimental observations with water and H 2s. If the reactions occur ionically, the effect of substituents should be significant. With a radical reaction pathway, the effect should be minimal. The effect of substituents on a reaction involving ionic intermediates can be most effectively studied by Hammett li f 1 t h" 44 If th 1 t f 1 k near ree-energy re a 1ons 1p. e p o o og vs. Hammett in a negative slope, that is Hammett p is negative, the rate determining step in-volves the process in which electron donating sub-stituents accelerate the reaction, either by stablizing intermediate or facilitating the leaving group. If p is

PAGE 43

30 positive, the rate limiting step is accelerated by electron withdrawing groups. Deviation from a straight line plot implies a change in overall reaction pathway as the nature of substituent is varied, or a shift in the rate limiting step within the overall reaction pathway. Corresponding for the substituents employed in our study are given in Table 8. All reactions were performed in a multireactor system at the US Department of Energy, Pittsburgh Energy Technology Center. Reaction conditions of for 3 hours at 4290 psi H 2o were employed in all cases. Due to the limited amount of reactor time avail-able to us at the Pittsburgh Energy Technology Center, only one sample was run in duplicate as a test of reproduciblilty (A#l, C#5). Inspite of the carefully controlled reaction conditions, the production of higher molecular weight compounds were inconsistent. Low molecular weight compounds were similar but product/internal standard ratios, as measured by in-tegrated area under the GC peaks, were inconsistent as well. Consequently, only qualitative discussions of the more interesting reaction pathways follows. The number of deuteriums incorporated into the products has been calculated by comparing M, M+l, M+2, 45 abundance ratios from the literature, with isotope

PAGE 44

31 Table 8 Hammett Values of Groups Used in the Reaction O"m O"p O"ind O"p+ O"pNH2 -0.16 -0.66 -0.12 -1.30 -0.15 t-Bu -0.10 -0.20 -0.07 -0.26 -0.13 CH3 -0.07 -0.17 -0.04 -0.13 H 0 0 0 0 0 CH30CO 0.37 0.45 0.34 0.46 0.64 EtOCO 0.37 0.45 0.21 0.46 0.64 CF3 0.43 0;54 0.41 0.61 0.65 NH3 + 0.86 0.60 0.61

PAGE 45

32 intensities reported as normalized to the intensity of M. The isotopic abundance ratios of reaction products are normalized to the highest intensity signal in the vicinity of the parent peak. When experimental M+1 value exceeded more than twice the literature value, it was assumed that some molecules had molecular weights which were increased by one, that is one deuterium was incorporated into it. Experimental M+2 was then normalized to experimental M+1 abundance ratios, and again compared with the literature value. When the M+2 value thus calculated exceeded more than twice the literature value, it was assumed that some molecules had molecular weight which were increased by two, and so on. There is no statistical basis for choosing twice the literature value as a criterion, but measured natural abundance ratios of the same compounds produced from different starting materials all fell within twice the literature value. The GC/MS results for all reactions are summarized in Appendix 2. 3-1 Substituted Bibenzyls where R H For the compounds where R= H, the reactions were run only in o2o.

PAGE 46

33 Toluene and substituted toluenes were the major low molecular weight products in all cases. Both com pounds were multiply deuterated (Appendix 2). The maximum number of deuteriums incorporated into these products do not correlate with substituent effects suggesting radical-like reactions. Stenberg (1980) indicated that water is not reactive as a hydrogen atom transfer agent under liquifaction conditions. His conclusion was based upon experimental evidence and the high homolitic bond energy of H-OH,4 as was discussed earlier. Inspite of this thermodynamic handicap, the incorporation of deuterium in our reaction products clearly suggests reaction with water. Such incorporation can be envisioned either radically or ionically, although the lack of corresponding hydroxyl compounds is puzzling. Hydroxy-substituted compounds may have been left in the aqueous layer, or may have polymerized to form high molecular weight compounds which were not identified at this stage. The most abundant components of the dichloromethane extract were deuterated starting materials. There was an observed trend to the maximum possible number of deuterium incorporated into the starting materials. That is, the more electrondonating

PAGE 47

34 Table 9 Product Distributions of Major Products OoH x-o-cH2CH3 X OH H OH H H20 0.22(1) 0.16 -NH2 020 NO NO NO NO H20 0.12 0.15 -CH3 020 NO NO NO NO H20 0.009 0.08 -H 020 0.062 NO 0.026 NO 50 40 H20 NO 0.017 -m-CF3 020 NO NO NO NO H20 NO -NO CH302C 020 NO NO NO NO (1) The numbers are the ratios of pentanollproduct, measured by thearea under the GC peaks. ND: not detected. number D: the number of possible deuteriums incorporated.

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35 Table 9 -continued Qca3 xVcH3 R OH H OH H H20 0.56 0.062 -NH2 020 NO 0.21 NO 0.12 3D 6D H20 0.27 -0.36 -CH3 020 trace 0.053 -3D H20 0.10 -0.32 -H 020 0.23 0. 13( 2 ) 0.15 0.13(2 ) 6D 3D 3D 3D H20 0.014 0.10 -m-CF3 020 0.069 0.16 0.053 0.064 6D 2D 3D 2D H20 0.13 0.083. -( -C02 H) CH302C 0.047 0.0685[ 020 0.18 0.14 0.0876D 3D trace 4 D (-C02H)4D (2) experimental value x 1/2

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36 Table 9 -continued starting materials rearranged compounds OH H OH H H20 0.84 OB -NH2 020 -1.44 NO NO SD H20 0.80 OB -CH3 020 1.85 OB NO 6D H20 1.01 -DB -H 020 1.51 2.39 DB NO 7D 3D H20 1.14 OB -m-CF3 020 1.34 L83 DB NO SD 2D H20 --NO CH302C 0.021 0.13 1D 020 (-C02H) 1 .35( -C02H) NO NO 3D 4D OB: observed. ND: not detected. number D: the number of possible deteriums incorporated

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37 Table 9 -continued cyclic compounds high m. wt. compounds OH H OH H H20 DB -DB -NH2 020 DB NO DB NO H20 DB -DB CH3 020 DB NO DB -H20 DB NO H 020 DB DB NO trace H20 ND -DB m-CF3 020 NO ND DB DB H20 NO -DB CH3D2C 020 NO ND DB NO 08: observed. ND: not detected.

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38 the substituents, the more deuterium that was incor-porated. Table 9 summarizes the major products. This would suggest that the electron donating group en-courages and stablizes the intermediates of the exchange process. Deuterium exchange may be envisioned by either radical or ionic pathways as illustrated in Scheme 6. Scheme 6 (R:X or H) R-@-cH2 xp-cH2CH2-@ 0 X -@-CH-CH2-@ D H D-0' Jr l 020 I D + x-Q-cH2CH2-@ + D OD e e H X -@-cH-CH2-@ l 020 D D If the reactions are radical, this would contradict Stenberg's conclusions and appear thermodynamically + H e + OD

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39 unfavorable. If ionic reactions are taking place, either aliphatic or aromatic substitutions are possible. Route B would be stablized by electron donating groups, but alcohol products would be expected and these have not been observed. Route C forms carbanion intermediates, hence electron withdrawing groups would be expected to stablize the intermediates. The electrophilic aromatic substitutions illustrated via route A agrees with the observed substituent effects, since electron donating groups would be expected to stablize the intermediate arenium ions. The deuterated products identified from these reactions are illustrated in Appendix 2. The formation of stilbenes from bibenzyl (IVd), and m-trifluoromethyl bibenzyl (IVe), are consistant with the radical mechanisms presented in Scheme 1 Phenanthrene, which was also observed, is also a possible product from radical reactions (Scheme 7).

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40 Scheme 7 (;Oi) f-(A) fH J I t.R H r R -r H ---7 (C)() The most intriguing reaction in this series was the reaction of the carboxylic acid methyl ester sub-stituted bibenzyl_(IVf). The most abundant dichloromethane soluble specie was the demethylated carboxylic acid (!Vg). The demethylation process is probably ionic, where water is acting as nucleophile (Scheme 8).

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41 Scheme 8 1 + ( IVg) (IVg) was also observed to decarboxylate to produce bibenzyl (IVd) as one of the major products. The decar-boxylation process can be envisioned either ionically, or radically (Scheme 9 and 10). Scheme 9 e o-c-{0;-cH 2CH2.0 0 D o .... 'o el D o-cQ-cH2CH2.0 II<) 0 l

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Scheme 10 --7 0 RD 42 l The maximum number of deuterium incorporated into biben-zyl produced from (IVf) was four. which was one more than the number of deuterium incorporated into the unreacted bibenzyl when bibenzyl was the starting com-pound. This suggests the substitution of a deuterium for the carboxylic moiety on the aromatic ring. 3-2 Substituted Bibenzyls where R = OH For the compounds where R = OH. the reactions were run in both H 2o. and o2o. There are two basic comparisons. One is the comparison between the products from the reaction in o2o when R = H (bibenzyls) and R OH (o-hydroxybibenzyls). Although strict quantitative

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discussions are not possible due to the poor reproducibility, simple comparisons were attempted. The other comparison is product distribution between reactions in the presence of H 2o and o2o. The products formed in each were similar. Generally, the 43 reactions proceeded more in H 2o than o2o; unreacted starting materials were less, and the. amount of reaction products were greater in H 2o. These results suggest the presence of a primary isotope effect. Every compound recovered from each reaction with o2o contained deuterium. The acidic hydrogen of the phenol was expected to be readily exchanged with deuterium from 0 20. Since phenolic hydrogens are well known hydrogen transfer agents in radical reactions,46 the observed distribution of deuterium through out the products was not surprising. The major low molecular weight products observed from a-hydroxy bibenzyls are: hydroxy toluene, sub-stituted toluenes, phenol and substituted ethyl ben-zenes. Hydroxy toluene and substituted toluenes are possible products of the bibenzyl thermolysis reaction. There was no clear indication of a substituent effect. Generally, the amount of products produced in H 2o were greater than in o2o.

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44 On comparing the thermolysis products between R = H, and R = OH, namely toluene and substituted toluenes from run A with a-hydroxy toluene and substituted toluenes from run C, there were no obvious trends in the number of deuteriums incorporated into the products. There were also no significant differences in the amount of products formed. These results demonstrate the dominance of radical thermolysis pathways even in the presence of supercritical water. Phenol and substituted ethyl benzenes are also possible products resulting from the cleavage of arylaliphatic bond. Neither compound was observed in the reaction, where R = H. The phenolic group could facilitate this cleavage, either ionically or radically as shown in Scheme. Alcohols, the expected products from ionic reactions were not identified. The radical fragments from the alternative homolitic cleavage may or may not react with o2o in order to incorporate deuterium. Unlike R = H, where o2o is the only possible deuterium source, the phenolic hydrogen will readily exchange with deuterium oxide resulting in a labile source of deuterium atoms. Upon comparing the amount of these compounds formed from the reactions with H 2o and o2o, the reactions with H 2o produced a larger amount of compounds. This would be expected if the formation of

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45 the keto tautomer was rate limiting. Within the reaction in the presence of H 20, the abundance of these products seemed to increase as electrondonating ability of sub-stituents increased. The reason for this trend is not obvious (Table 8, and Appendix 2-C). Scheme 11 x-o-cH2CH2p Hfo H x-o-cH2CH2'? 0 1 rad1cal () x-o-cH2CH2 + H x-o-cH2CH2 + l RH x-o-cH2CH3 (not found) + R Comparison of the amount of unreacted starting materials was consistant with previous discussions. More starting materials were observed in o2o than in H 2o, and more when R = H, than R = OH. More deuterium incorporation was observed with increasing electrondonating ability, but the trend was less clear than for R = H. 9 0 1 p

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o-Hydroxyethylbenzene was found only from the reaction of p-amino-a'-hydroxybibenzyl. Since the electrondonating ability of the amino group is larger than that of a hydroxyl group, a reaction such as that illustrated in Scheme 12 becomes feasible. Scheme 12 HO l Rearranged starting reactants were observed in 116 the p-NH2 p-CH3 H, and m-CF3 substituted cases, where R = OH. A proposed reaction pathway is illustrated in Scheme 13.

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Scheme 13 ----+) X Cyclization seems to have occurred in bo,th H 2o and o2o where the substituents were p-NH2 p-CH3 and H groups. No cyclization products have been identified 47 where substituents were eledtronwithdrawing groups. Two possible pathways for these products are illustrated in Scheme 14. The reaction of p-amino-a'-hydroxybibenzyl in o2o varied significantly from all other reactions. The amount of internal standard, pentanol, recovered was very small and the major product observed had a presumed parent ion of a mass of 394. The explanation for the anomaly remains elusive.

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48 Scheme 14 --7 (tA) X 1... X H 0 X H 0 lk l (JC':O 0 0 X X H Alternative () .X) ----7 (:(;)0 X H 0 X t.,:O 0 X H H e 't__....B l R() H!i.l' (JC':O X 0 0 X H te8

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49 3-3 Future Plans The establishment of quantitative reliability is our major priority. To this end, we recently purchased a Parr 22 ml microreactor which in other experiments has lead to highly reproducible results. Once quantitative reliability has been established, the suggested trends from this work can be confirmed. Particular focus will be on confirming the effect of substituents on deuterium exchange. Other ambiguous reaction pathways will also be tested through the use of radical scavengers such as cresol or tetralin. Alternative Lewis acid catalysts may also be added in an attempt to enhance ionic reactions. 3-li Conclusions The object of this thesis was to study the role of water under coal liquifaction conditions using substituted bibenzyls and a'-hydroxybibenzyls as coal models. The series of substituted bibenzyls and a'hydroxybibenzyls were synthesized via Wittig reaction followed by hydrogenation. The substituents synthesized for both bibenzyls and a'hydroxybibenzyls were p-NH2 p-CH3 H, m-CF3 and p-CH3o2c.

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50 The model compounds were reacted with H 2o or o2o under 4290 psi (0.30 kbar), at 400C for 3 hours. Thermolysis pathways dominated the reaction of substituted bibenzyls. The thermolysis products and recovered starting materials were observed to undergo deuterium exchange. The observation of exchange implies that previously unknown reactions are tak-ing place between supercritical water and the substituted bibenzyls. Mechanisms for these reactions were suggested. In the case of p-CH3o2c, demethylation, decarboxylation and deuterium substitution dominated. This suggests an ionic pathway. Comparison of the product distribututions between H 2o and o2o for the substituted a' hydroxybibenzyls indicates a primary isotope effect, although the thermolysis pathway again predominated. The a'-hydroxybibenzyls exhibited more deuterium exchange than with the simple bibenzyls. This may be due to the enhanced hydrogen transfer ability of phenolic hydrogen under radical reactions. The tautomerization pathways contributed significantly to the product distributions. They also exhibited a primary isotope effect which suggests that tautomerization is rate limiting. 2-Ethyl-4-substituted diphenyl ethers were observed and are possibly produced through the rearrangement of certain substituted a'-hydroxybibenzyls. Cyclization of p-NH2

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p-cH3 H, substituted a'-hydroxybibenzyls to dibenzodihydrooxepane was also observed. ( 51

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CHAPTER IV EXPERIMENTAL When anhydrous solvents were required, the solvents were dried over 3-A molecular sieves prior to use. All commercially available reagents were used without further purification. Melting points were measured on a Mel-Temp electrothermal melting point apparatus manufactured by Laboratory Devices. The thermometer used was uncalibrated and the reported melting points were not corrected for high altitude. GC/MS analysis were performed on a Hewlett Packard model 5890A mass selective detector. A typical temperature program consisted of elevating the temperature from 80C to 250C at 8C/min, with 1.6 min solvent delay. IR spectra were recorded on Perkin-Elmer 7108 infrared spectrophotometer.

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53 4-1 Synthesis 4-1-1 a-Bromo-p-toluic acid methyl ester In an Erlenmeyer flask, a-bromo-p-toluic acid (10 g, 0.0465 mol) was dissolved in 20 mL THF. The flask was placed in a dry ice/acetone bath. Ethereal diazomethane generated from 13.93 g (0.0651 mol) p-toluenesulfonylnitrosamide, was distilled into the flask. After distillation was completed, the flask was removed from the dry ice/acetone bath and allowed to come to room temperature while stirring. The completion of the reaction was detected by the disappearance of yellow color and vigorous foaming. After rotary evapora-tion of the solvent, a white solid was obtained (11 .96 g, 112 %, mp 30-160C). M/e (relative ionization): 228 + + + [18.6, M ], 197 [19.7, MCH3J, 149 [100.0, M -Br], 90 [78.0, 149 co 2cH3J. 4-1-2 Salicylaldehyde benzyl ether Benzyl bromide (15 mL, 0.126 mol) and potassium carbonate (18 g, 0.13 mol) were slowly added to a solu-tion of benzaldehyde (12.9 mL, 0.12 mol) in 75 mL acetone at room temperature. After refluxing for 3.5 hrs, the entire mixture was taken up in a large excess

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of H 2o at which point, a yellow oil separated. The oil was extracted with ether and washed with a sodium car-bonate solution. The solvent was evaporated and the oil distilled at 174-185C, 3 torr, yielding a yellow oil, 17.2 g (67.5 %). M/e (relative ionization): 212 [10.5, + + M ], 183 [21.0, MCHO], 121 [24.5, PhCHO], 91 [100, PhCH2J. --1-3 Salicylaldehyde acetyl ether Acetic anhydride, 150 mL, and potassium car-bonate, 150 g, was added to the solution of salicylal-dehyde (100 g, 0.82 mol) in 500 mL ether. The mixture was stirred at room temperature for 30 min, after which, solids were filtered off. Following rotary-evaporation of ether, the oil was taken up into water at which point a white solid separated. Recrystallization from petroleum ether gave 56 g (46 %) white needle, mp 36.5380C (38C).18 --1-Salicylaldehyde tetrahydropyranyl ether Dihydropyran (6.3 g, 0.075 mol) and pyridinium-p-toluenesulfonate (1.26 g, 0.05 mol) were added to a solution of salicylaldehyde (6.1 g, 0.05 mol) in 150 mL dichloromethane. The solution was stirred at room tern-

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55 perature for 4 hrs, 24 hrs, and 48 hrs. GC/MS of reac-tion aliquots indicated that only the reactants were present. 4-1-5 Pyridinlum-p-toluenesulfonate (PPTS) p-Toluenesulfonic acid monohydrate (28.5 g, 0.15 mol) was added to pyridine (69.5 mL, 0.74 mol) with stirring at room temperature. After stirring for 20 min, the excess pyridine was rotary-evaporated to produce a white solid. Recrystallization from acetone gave, white crystals, 37.7 g (73.7 %), mp 116-118C (120C).34 All bibenzyls were synthesized via phosphonates and stilbenes, as exemplified below by the synthesis of p-methyl-bibenzyl. 4-1-6 Diethyl-p-methylbenzylphosphate (Ic} a-Bromo-p-xylene (10.0 g, 0.055 mol) was dripped into triethylphosphite (9.6 g, 0.058 mol) with stirring over a period of 25 min at room temperature. The solu-tion was refluxed over night. Distillation at 107-122C, 3 torr, gave 12.2 g (86.5 %) of a clear colorless liq-+ uid. M/e (relative ionization): 242 [12.2, M ], 213 + + [5.2, M-Et], 105 [100, M -(EtO)lO]. This material was

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56 used without further purification. (IIc) Diethyl-p-methylbenzylphosphonate (Ic) (3.62 g, 0.015 mol) was dripped into the mixture of sodium hydride (0.31 g, 0.015 mol) in 50 mL dry dimethylethoxide with stirring at room temperature, followed by slow addition of benzaldehyde (1.5 g, 0.015 mol). After refluxing for 2 days, the mixture was taken up in a large excess of water, at which point, a taline solid was obtained. Recrystallization twice from 95% ethanol gave 2.08 g (71.5 %) of light yellow plates, mp 117-118C. (IVc) (IIc) (0.954 g, 3.18 mmol) was dissolved in 200 mL absolute ethanol. Palladium on carbon was added as catalyst. Following hydrogenation in a Parr hydrogenator at room temperature for 2-4 hrs, at 30 psi, the catalyst was filtered and the solvent evaporated to yield a tan solid g, 3.02 mmol (94.9 %)), which was pure by GC/MS. M/e (relative ionization): + + 196 [25, M ], 105 [100, M mp 25-26C 47

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57 p-Bromobibenzyl Bromine (4.31 g, 0.024 mol) was added slowly to the solution of stilbene (5 g, 0.027 mol) in 20 mL acetic acid, containing 0.05 g iron filing. The mixture was heated at 63C, for 4 hrs. The insoluble materials were filtered, and the solution was neutralized with 10 % sodium hydroxide, followed by extraction with ether. Rotary-evaporation of the ether gave a dark yellow oil containing 2 different isomers of monobromostilbene, stilbene and a small amount of dibromo substituted compounds, as evidenced by GC/MS. The desired product was not isolated. p-Nitrobibenzyl A) By hydroboration reduction. Borane-pyridine complex (0.12 g, 1.3 mmol) was dripped into the solution of p-nitrostilbene (0.3 g, 1.3 mmol) in 5 mL dry diglyme at room temperature. The mixture was refluxed at 210C for 30 min. After cooling to room temperature, propionic acid (0.078 g, 1.3 mmol) was added. The mixture was further refluxed for 30 min. The resulting mixture contained p-nitrobibenzyl and p-nitrostilbene with a GC peak area ratio of 0.56. Refluxing for an additional 60 min increased the amount of side products, resulting in

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a decrease of p-nitrobibenzyl/p-nitrostilbene ratio to 0.36. The products were not isolated. 58 B) By diimide reduction. A solution of ptoiuenesulfonyhydrazide (0.57 g, 3 mmol) in 3 mL triglyme was slowly added to a solution of p-nitrostilbene (0.3 g, 1.3 mmol) in 7 mL triglyme, at room temperature. As the temperature raised slowly, the solution started to foam. In 10 min, the temperature reached 170C at which point, the foaming subsided. GC/MS of the mixture indicated the presence of 24 compounds including pnitrobibenzyl. The GC peak ratio of p-nitrobibenzyl/pnitrostilbene was 1 .73. Purification was not attempted. C) By hydrogenation with rhodium catalyst. pNitrostilbene was dissolved in 100 mL/50 mL, ethanol/THF, to which rhodium on alumina (0.01 g) was added as catalyst. After shaking at room temperature, for 2 hrs. under 30 psi H 2 in a Parr hydrogenator, the catalyst was filtered. As analyzed by GC/MS, the solution contained p-nitrobibenzyl, p-nitrostilbene, and two other products. The GC peak area ratio of pnitrobibenzyl/p-nitrostilbene was 0.46. Purification was not attempted.

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59 D) By oxidation with peroxide. 90 % Hydrogen peroxide (0.744 mL, 0.0279 mol) was added slowly to 12 mL dichloromethane at room temperature, without stirring. The solution was then placed in an ice bath, followed by slow addition of trifluoroacetic anhydride (3.9 mL, 0.0279 mol) with stirring. The solution was stirred for 30 min as it was brought to room temperature at which point p-aminobibenzyl (1.1 g, 5.58 mmol) in 10 mL dichloromethane was slowly introduced by dropwise addition. After refluxing for 1 hr, the cooled solution was taken up in 20 mL water. The organic layer was washed with water, 10 % sodium carbonate, and again with water. After treatment with activated charcoal, and drying with magnesium sulfate, the solvent was evaporated. The dark brown oil thus obtained (0.34 g) contained p-nitrobibenzyl and p-aminobibenzyl with GC area ratio of 1.21. Four other minor products were also observed. Separation was not attempted. E) By cuprous iodide coupling. Cuprous iodide (1.63g, 8.5 mrnol) and triethylphosphite (0.28 g, 1.71 mmol) were added to a solution of p-nitrobenzylbromide (2.0 g, 7.66 mmol) in 20 mL THF. The mixture was cooled to -29C with an o-xylene/liquid nitrogen bath. A THF solution of benzyl magnesium bromide (11.5 mmol), syn-

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60 thesized from benzyl bromide (1 .52 g, 12.mmol) and magnesium (0.32 g, 13.2 mmol), was added slowly. The mixture was brought to room temperature while stirring for 2 hrs, after which 20 mL of ether was added. The mixture was washed.with sodium chloride solution. The light yellow solution thus obtained contained four compounds by GC/MS, including p-nitrobibenzyl, bibenzyl, p-nitrobenzylbromide and one other minor side product. The GC peak area ratio of p-nitrobibenzyl/bibenzyl was 0.26. Purification by preparatory silica gel TLC was attempted. Out of 27 bands which as been separated, only one band contained the desired product in insignificant yield. 4-2 Reactions A multireactor system at the US Department of Energy, Pittsburgh Energy Technology Center was employed for the reactions. The system consists of five in-"dividual microautoclaves, each of approximately 45 mL 48 capacity and attached to a single yoke. The entire assembly was immersed rapidly into a preheated, fluidized sand bath, allowing it to heat-up to reaction temperature in 4-6 minutes. Immersion in a second fluidized sand bath held at room temperature provided

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61 rapid quenching. The autoclaves were agitated by a rapid horizontal-shaking motion, assuring good mixing of heterogeneous, multiphase mixtures. Individual thermocouples allowed continuous temperature monitoring of each microautoclave. The reaction conditions were chosen so that 2.6 mmole of each compound was reacted in presence of 4.3 mL H 2o or containing 2 mL pentanol/93.4 mL H 2o, or 2 mL/100 g o2o, as internal standard. T-his resulted in the mole ratio of the reactant to standard of 2 : 1. Pen tane! was selected as standard since its solubility in water (16.6 g/100 mL at 20C) was just large enough to ensure the desired concentration, yet would favor partition into dichloromethane upon work up. All reactions were run at 400 C for 3 hrs. The pressure at reaction temperature was not measured directly in these experiments. Using van der Waal's equation, the partial pressure of water was estimated as 4290 psi. The density of supercritical water was 0.095 g/mL. After the reaction, the interior of the reactor was washed several times with a total of 5 mL dichloromethane. The dichloromethane, the aqueous mixture thus obtained was shaken so that equilibrium of the products between two layers was achieved. Each

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62 dichloromethane layer was analyzed by GC/MS using two different GC columns. Methyl silicone coated 25 m capillary column was used for lower molecular weight compounds under standard conditions, and 12 m, DV I capillary column for higher molecular weight compounds, with temperature elevation of 8C/min, from 80C to 300C. Table 10 summarizes the reaction.

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63 Table 10 Summaries of the Reactions Run X R System A CH3o2c OH Vf D 2 D 2 m-CF3 OH Ve D 2 D 3 H OH Vd D 2 D 4 CH3 OH Vc D 2 D 5 NH3 OH Ve D 2 D B CH3o2c OH Vf H 2 0 2 m-CF3 OH Ve H 2 0 3 H OH Vd H 2 0 4 CH3 OH Vc H 2 0 5 NH3 OH Ve H 2 0 c NH3 H IVe D 2 D 2 H H IVb D 2 D 3 CH3o2c H IVf D 2 D 4 m-CF3 H IVe D 2 D 5 CH3o2c OH Vf D 2 D

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REFERENCES 1. a) J. B. Hannay, J. Hogarth, Proc. R. Soc. London, 29, 324 (1874) b) J. B. Hannay, J. Hogarth, Ibid., 30, 178 (1880) 2. M. A. McHugh, V. J. Krukonis, "Super Critical Fluid Extraction", Butterworths (1986) 3. G. A. Wiltsee Jr., Quarterly Technical Progress Report for the Period July 1983 -Sept. i983, Prepared for the u. S. Department of Energy, Office of Fossil Energy, Under Cooperative Agreement DE-FC01-38FE60181,17 4. V. I. Stenberg, R. D. Hei, P. G. Sweeny, J. Nowack, Am. Chern. Soc. Div. Fuel Chern. ?reprints, 29(5), 63 (1984), and references cited there in. 5. G. v. Deshpande, G. D. Holder, A. A. Bishop, J. Gopal, I. Wender, Fuel, 63, 956 (1984) 6. P. Barton, Ind. Eng. Chern., Process Des. Dev., 22 589 (1983) 7. D. s. Ross, J. E. Blessing, Q. C. Nguyen, G. P. Hum Fuel, 63, 1206. (1984) 8. D. S. Ross, Q. C. Nguyen, G. P. Hum, Ibid.,63, 1211 (1984) 9. M. E. Paulaitis, M. T. Klein, A. B. Stilles, DOE Quarterly Report, DE-FD22-82PC50799, July-Sept. (1983) 10. B. D. Blaustsin, B. C. Bochrath, H. N. Davis, M. A. Mikita, Am. Chern. Soc. Div. Fuel Chern. ?reprint 30(20), 359 (1985) 11. M. A. Mikita, H. T. Fish, Ibid., 31 (4), 56 (1986) 12. H. T. Fish, M. A. Mikita, Abstact Am. Chern. Soc. 193rd National Meeting, April 6; 1987, Denver Colorado

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65 13 0 P. s. Virk, Fuel, 58 J 148 (1979) 1 4 0 R. A. Miller, s. E. Stein, Am. Che;m. Soc. Div. Fuel Chern. ?reprint, 24 (2) J 271 ( 1979) 15. L. w. Vernon, Ibid., 24(2), 143 (1979) 16. Y. Sato. Fuel, 58, 318 ( 1979) 17. D. C. Cronauer, W. L. Kehl, Ind. Eng. Chern. Fundam., 17, 291 (1978) 18. B. M. Benjamin, Fuel, 57, 378 (1978) 19. D. D. Whitehurst, EPRI Report AF-480, 9-44 (1977) 20. R. E. Miller, S.C. Stein, J. Phys. Chern., 85, 580 ( 1 981 ) 21. R. Livingston, H. Zeldes, M.S. Conradi, J. Am. Chern. Soc., 101, Li312, (1979)" 22. D. s. Ross, J. E. Blessing, in "Coal Liquifaction Fundamentals, ACS Symposium Series 139", D. D. Whitehurst ed., 301, (1980) 23. S. W. Benson, H. O'Neal, "Kinetic Data on Gas Phase Unimolecular Reactions", National Bureau of Standards, NSRDS-NBS21 (1970) 2Li. L. M. Vernon, Fuel, 59, 102 (1980) 25. M. L. Poutsma, Ibid., 59, 335 (1980) 26. Y. Kakemura, H. Itoh, K. Ouch!, Ibid., 80, 379 (1981) 27. Fieser and Fieser, Reagents for Organic Synthesis vol.1, 191, John Wiley (1967) 28. G. Wittig, Organic Syntheses, vol LIO, 66 (1960) 29. G. Koslapoff, "Organophosphorus Compounds" Chapt. 7, John Wiley (1950) 30. F. A. Carey, R. J. Sunberg, "Advanced Organic Chemistry, second ed.,Part A", Plenum Press (198Li)

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31. T. Makin, N. Nierenstein, J. Am. Chern. Soc. 53 239 (1 931) 32. N. Miyashita, A. Yoshikoshi, P. A. Grieco, J. Org. Chern., 42, 3772 (1977) 33. J. H. Van Boom, Synthesis, 169 (1973) 34. C. B. Reese, R. Saffhill, J. E. Sulston, J. Am. Chern. Soc., 89, 3366 (1967) 35. M. Miyano, et al., Nippon Nogei Kagaku Shi, 34(8) 683 (1960) 36. R. E. Litz, et. at., J. Org. Chern., 12, 617 (1947) 66 37. H. C. Brown, K. Murray, J. Am. Chern. Soc., 81, 4180 ( 1 959) 38. Fieser and Fieser, Reagents for Organic Synthesis vel. 8, 50 (1980) 39. G. E. Ham, W. P. Coker, J. Am. Chern. Soc., 194 ( 1 964) 40. R. E. Dewey, E. E. van Tamalen, J. Am. Chern. Soc. 83, 3729 (1 961) 41. G. E. Pagano, w. D. Enmons, Organic Syntheses, vel. 49, 47 (1969) 42. H. Alper, ed., "Transitionmetal Organometallics in Organic Synthesis", vel. 1, 114, Academic Press (1976) 43. H. U. Wagner, R. Gompper, in "The Chemistry of the Quinoid compounds, Part 2", S. Patai, ed., John Wiley, 1145 (1974) 44. P. Sykes, "A Guide Book to Mechanism in Organic Chemistry, sixth ed.", 358, Longman (1986) 45. R. M. Silverstein, G. c. Bassler, T. c. Morrill "Spectrometric Identifaication of Organic Compounds, fourth ed.", John Wiley (1981) 46. Y. Kamiya, T. Yao, S., Oikawa, in "Coal Liquifaction Fundamentals, ACS Symposium Series 139", D. D. Whitehurst ed.,291, Am. Chern. Soc. (1980)

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47. R. L. HinMan, K. L. Marnm, J. Am. Chern. Soc. 81, 3294 (1959) 48. R. R. Anderson, B. C. Bockrath, Fuel, 63, 329 (1984) 67

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Appendix 1 68 HOMOL VT I C BOND STRENGTH H-OH eromet i c C-H prim. C-H sec. C-H benzylic C-H 11 9.0 < 1) keel /mole 110.6 (2 ) 97.9 (2 ) 94.6 ( 2 ) 81.9 (2 ) bi benzyl c-c 61.8 ( 2 ) (57) (4 )) (1) J.McMurry, "Organic Chemistry, 2nd ed.", Brooks and Cole (1988) (2) S.'w' .Benson, "Thermochemical Kinetics, 2nd ed." 'w'iley, ( 1976) (3) D .F .McMillan, D .M .Golden, Annu. Rev. Phy s. Chem., 33 493 (1982) (4) D.S.Ross, J.E.Blessing, "Coal Liquifaction Fundamentals: ACS Symposium Seires 139", Am. Chem. Soc., 301 (1980)

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69 Appendix 2 R Anelysis of the Dichloromethane Extrecteble Compounds by GC/MS m.wt. (1) Compound i dent i f1 ed no. of D X formula i nco r po rated Mess spectrum dete (2) m/e [relative intensity] Mass Literature values <3 ) retention sample H20 time Exp. values 1 (5 ) no. i nt. stand ( 4 ) comp retention sample D20 time Exp. values 2 no. int. stand comp (1) Suggested strtusture is drawn with [ ] (2) Mass spectrum data of the raction in the presence of water. (3) R.M.Silverstein1 G.C.Bassler 1 T .C.Morril11 "Spectrometric lndentification of Organic Compounds 1 4th ed. "1 John Wiley and Sons ( 1 981 ) (4) The ratio of integrated GC peak areas. (5) Mass abundances are normalized to the highest peak at the vicinity of the parent peak

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70 AppendiX 2 -A 108 Q-cH3 C7HeO OH CH3C1 09[53, M+ L 1 07[1 00, M+-HL 90[32, M+H20] I II 0 77[42, B] 107 109 109 110 111 112 113 114 100 77.3 0.43 5.60 e H20 0.129 100 97.7 10.4 5.21 78.5 0.89 100 76.0 40.1 OH A D20 6D 0.047 100 52.8 5.02 3.2 25.4 77.5 100 94.1 42.0 12.7 c D20 6D 0.097 100 30.0

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71 Appendix 2-A (continued) 94 Q-oH C6H60 CH3CII 0 94 95 96 97 98 99 100 6.62 0.38 B H20 ND OH A D20 ND 4.21 100 91.3 22.1 cs D20 SD 0.013 100 24.0

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72 Appendix 2-A (continued) 136 CaHaO 0 CH3C-136[59, M+], 119[51, M+OH], 91 [100, M+-C02Hl II 0 135 136 137 138 139 140 141 100 8.85 0.75 8'*1 H20 6.3 100 10.6 OH A'*1 D20 4D 84.0 100 87.3 29.5 71.4 100 81.8 50,2 18.1 c D20 5D 100 35.7

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73 Appendix 2-A (continued) 198 H-o-CH2CH2-) c14H14 o H-0 CH3C198 [23 I M+ L 1 07 [ 1 00 I M + .0' CH2] II 0 198 199 200 201 202 203 204 205 100 15.4 1.30 13.75 a H20 0.040 100 17.6 .. 13.72 OH A 020 70 0.054 100 77.6 13.71 75.1 100 76.6 64.2 cs 020 70 0.022 100 83.5

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74 Appendix 2-A (continued) 226 H-a-c-o-cH2CH2-() other II u n; dent; f; ed c1sH14o2 peeks CH3CII 0 226 227 228 229 100 16.5 1.68 8 H20 NO v OH A01 D20 NO v 16.05 cs D20 0.021 100 100 63.2 30 v

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A p p e n d X 2-B H H H H NH2 C*l H C*2 CH30C II 0 C*3 m-CF3 c 92 c 7 H 8 90 1.94 020 0.205 92 C7He 90 1.94 020 0.264 92 C7He 90 1.94 020 0.180 5.9 92 C7He 90 1.94 020 0.160 5.0 75 @-cH3 3D 91 92 93 94 95 96 100 7.69 0.25 27.6 100 86.8 23.2 5.4 0.8 100 23.2 13.1 @-cH3 3D 91 92 93 94 95 96 100 7.69 0.25 22.7 90.7 100 42.5 10.4 1.4 100 23.0 3.3 @-cH3 3D 91 92 93 94 95 96 100 7.69 0.25 33.7 100 94.2 38.6 10.2 1.8 100 26.0 4.6 @-cH3 3D 91 92 93 94 95 96 100 7.69 0.25 37.5 100 86.0 24.1 3.0 100 28.0 3.4

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A p p e n d i )( 2-B cont. H H H H NH2 c 020 H c 020 CH30C II 0 c 020 m-CF3 c 020 107 c 7 H 8 0 107 5.34 100 0.121 3.4 136 c8H8o2 136 8.32 100 0.140 41.5 160 C8H7f3 159 2.22 0.064 14.9 76 NH2 -@-cH3 5D 108 109 11 0 111 112 113 7.73 0.46 15.4 61.8 100 61.8 30.7 7.7 100 49.6 12.0 Hoc-@-cH3 II 0 4D 137 138 139 140 8.85 0.75 100 97.8 46.5 14.5 100 31.2 CF3 2D 160 161 162 163 100 8.76 0.34 57.2 100 46.5 7.9 100 11.2

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A p p e n d )( 2-B cont. H H H H NH2 c 020 H c 020 CH30C II 0 c 020 m-CF 3 c 020 77 197 NH2-@CH2CH2-@ C14H15N 50 197 198 199 200 201. 202 203 204 14.48 100 15.8 1.16 1.440 6.3 11.4 64.3 100 91.7 45.8 12.4 2.9 100 27.0 6.3 182 H-@CH2CH2-@ C14H14 3D 179 180 1 81 182 183 184 185 186 11 .1 8 100 15.4 1.1 0 2.387 60.4 100 100 40.7 7.4 100 18.2 240 CH 2 CH 2 -@ 0 C16H1602 10 240 241 242 243 11.15 100 17.6 1.86 0.245 100 41.0 12.6 5.4 100 30.7 13.2 250 C15H13 f3 CF3 20 248 249 250 251 252 253 254 11.06 100 16.4 1.26 1.832 100 66.2 44.4 11.1 1.8 100 25.0 4.1

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A p p e n d 1 X 2-B cont. H H H H NH2 ct D20 H C'*2 D2D 162 CH30C u 0 C14H14 11 .15 c D20 0.245 m-CF3 c D20 78 H-@CH2CH2-@ 4D 160 181 162 163 164 165 166 187 100 15.4 1.10 8.5 5.6 13.2 65.0 100 50.5 19.0 5.5 100 37.6 1 0.1

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A p p e n d 1 )( 2-B cont. H H H H NH2 C#l 020 H c 020 CH30C II 0 c 020 m-CF3 c 020 79 226 CH2CH2-@ 0 C15H1402 40 226 227 228 229 230 231 16.1 B 100 16.5 1.68 1.352 48.3 100 93.2 52.8 23.6 6.5 100 27.5

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A p p e n d X 2-B cont. H H H H NH2 C'*1 020 H C'*2 020 CH30C II 0 C'*3 020 m C'*4 020 80 180 H-@-CH=CH-@ c14H12 10 176 177 178 179 1.80 181 182 13.14 100 15.3 1.09 11.8 7.8 49.7 100 100 49.9 11.8 0.086 100 23.6 248 c15H11F3 CF3 10 247 248 249 250 13.0 100 16.4 1.25 26.3 100 53.1 12.8 0.025 100 24.2

PAGE 94

A p p e n d X 2-B cont. H H H H NH2 c 020 H c 020 CH30C II 0 c 020 m-CF3 c 0 20 81 176 c14H1 o 2D 176 177 178 179 160 13.93 100 15.3 1.09 39.4 19.9 100 51.9 39.4 0.031 100 75.9

PAGE 95

A p p e n d X 2-B cont. H H H H NH2 c 020 H c 020 CH30C II 0 c 020 m-CF3 c 020 82 197 C14H15N ( NH2 -@-CH CH3 J @ 40 195 196 197 198 199 200 201 14.75 100 15.8 1.16 0.033 7.6 23.2 46.8 100 81.8 34.3 14.0 100 41.9

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A p p e n d j X 2-B cont. H 83 30 195 196 197 198 199 200 201 202 16.56 ct __ 1_5._B __ 1._16 __________ H CH30C II 0 0.264 6.2 21.2 47.9 100 97.8 46.6 12.0 2.3 100 25.7 4.9 H c-3 H c 4 o 2 o 1-------+----------------------------_,

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84 Appendix 2 -C 160 CeH7F3 CF3 30 CF3 160 [32, M+l 141 [to,M+;. Fl, 91 !too,M+-cF3l 158 159 160 161 162 163 100 8.76 0.34 B H20 2.23 4.5 31.8 100 7.7 0.100 OH 2.23 A 020 22.0 85.1 100 37.1 7.1 0.053 100 18.7 92 @-cH3 C7H8 30 H 92 [51, M+ L 91 [100, M+-H] 89 90 91 92 93 94 95 96 100 7.64 0.25 B H20 1.95 100 50.7 6.1 0.006 0.321 100 12.1 1.3 OH 1.94 A 020 1..6 3.4 17.8 86.9 tOO 52.5 15.5 2.2 0.145 100 29.5 4.2

PAGE 98

85 Appendix 2-c (continued) 174 SQ,>-cH 2CH3 CgHgF3 CF3 CF3 174 [25, M+L 159 [100, M+-CH3) 155 [ 11 ,M+Fl 105 [18, M+-CF3] 174 175 176 100 9.87 0.43 6'*2 H20 3.13 100 0.017 OH A'*2 020 NO 106 @-cH2CH3 CaH1o 40 H 1 06 [24' M+ L 91 [ 1 00' M+ -CH3 I 105 106 107 108 109 110 100 8.80 0.34. 6'*3 H20 2.76 21.3 100 19.1 0.080 OH 2.74 A'*3 020 30.7 100 58.3 26.2 0.026 100 44.9

PAGE 99

86 Appendix 2-c (continued) CF3 B H20 OH A 020 94 @-oH C5H50 40 H 94 [100, M+ ),66 [50,Cp] 94 95 96 97 98 99 100 6.62 0.38 B H20 4.27 100 10.9 0.009 OH 4.13 A 020 91.3 100 16.5 0.062

PAGE 100

86 Appendix 2-c (continued) CF3 B H20 OH A 020 94 @-oH C5H50 40 H 94 [100, M+], 66 [50, Cp] 94 95 96 97 98 99 100 6.62 0.38 B H20 4.27 100 10.9 0.009 OH 4.13 91.3 100 16.5 A 020 0.062

PAGE 101

87 Appendix 2-c (continued) 108 <9(-oH C 7 H 6 0 CH3 CF3 60 108 [100 1 M-+), 107 [ 98 1 M+H), 90 [311 M+H20] 77 [55 I B.] 107 108 109 110 111 112 113 114 100 7.73 0.46 B H20 5.21 98.3 100 12.2 0.026 OH 5.14 12.5 A 020 57.4 75.8 100 65.6 28.5 0.064 100 43.4 108 <9(-oH CH3 C 7 H 8 0 50 H 108 [1001 M .. ], 107 [76 IM+H], 77 [50 I B.] 107 108 109 110 111 112 113 114 100 7.73 0.46 B H20 5.16 75.6 100 13.2 0.102 OH 5.07 A 020 2.3 16.3 53.9 100 76.7 32.9 11.1 0.227 100 42.9 14.5

PAGE 102

88 Appendi>< 2 -c (continued) 266 CF3 HO CF3 Cts H13 F30 50 266 [ 7. M+ L 159 [6, M+-CH2-Ph-OH ] 107 [1 00, M+-CH2-Ph-CF3] 266 267 268 269 270 271 272 273 100 16.5 1.47 B62 H20 13.64 100 20.6 1.5 1.143 OH 13.62 A62 020 50.0 100 81.3 31.2 7;8 1.6 1.341 100 25.2 5.2 196 HO C14H140 70 H 198 [ 15, M+L 107 [ 1001 M+-CH2-Ph ]1 91 [ 27. M+-CH2-Ph-OH ] I 77 [ 20 I Ph. ] 198 199 200 201 202 203 204 205 206 100 15.4 1.30 B63 H20 13.70 100 24.9 3.6 1.012 OH 13.69 A63 020 21.4 23.9 23.9 54.9 100 100 53.3 18.2 3.2 1.508 100 15.6

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89 Append1x 2C(continued) 266 ( J CF3 CH2CH3 CF3 Cls H13 F30 60 266 [48, M+], 251 [ 100, M+CH3), 231 [ 23,251-HF 1 181 [11, 251 -CF3 1 266 267 268 269 270 271 272 273 100 16.5 1.47 B-2 H20 13.21 100 19.8 0.048 OH 13.18 A 020 3.7 38.2 100 98.4 50.2 16.8 4.7 0.171 100 33.2 9.3 198 ( @ro-i)Q) J c,4H14o CH2CH3 60 H 198 [59, M+ ), 183 [ 1 00, M+CH3 1 165 [ 41 M+-331 77 [ 33, Ph 1 198 199 200 201 202 203 204 205 206 100 15.4 1.30 B H20 13.16 100 20.8 0.042 OH 13.10 A 020 5.6 12.3 45.5 98.3 100 80.7 24.8 5.8 0.210 100 30.7 7.1

PAGE 104

90 Appendix 2 -c (cont 1 nued) CF3 B#2 H20 OH A#2 020 194 C14 H10 0 30 H 194 [ 100, M+ L 165 [62, M+CHO] 194 195 196 197 198 100 15.4 1.29 B#3 H20 13.29 100 21.6 o:o36 OH 13.26 A#3 020 20.9. 100 27.8 0.033

PAGE 105

91 Appendix 2 -c (cant i nued) CF3 B.-2 H20 OH A.-2 020 194 [@C@J c14 H10 o 5D H 194 ( 100, M+ ], 165 [62, M+CHO] 1 07 ( 39 I CH2-PH-OH J 194 195 196 197 199 199 200 100 15.4 1.29 B.-3 H20 13.97 100 21.6 0.053 OH .95 A.-3 020 75.0 100 97.5 45.9 13.0 0.029 100 52.! 14.9

PAGE 106

92 Append1x 2 c CH3 6#4 H20 OH A#4 020 93 @-NH2 C 6 H 8 N NH2 93 [ 100, M+), 66 [61, Cp] 91 92 93 94 95 100 6.98 0.21 B#S H20 3.99 2.4 162 100 10.3 0.7 0.062 OH A#S 020 NO

PAGE 107

93 Appendix 2c (continued) 106 CH3-@-CH3 CH3 C5H1o 3D 106 ( 37, M+ ], 91 [ 1001 M+-CH3] 102 103 104 105 106 107 108 109 100 8.80 0.34 B H20 2.84 3.6 16.7 5.4 57.6 100 10.2 0.364 OH 2.86 A 020 23.1 50.3 100 86.9 28.4 0.053 100 32.7 107 NH2-@-CH3 C7HgN NH2 1 07 ( 65 I M+ ], 1 08 ( 1 00 I M+-H ]1 77 (16,Ph] 106 107 108 109 100 8.09 0.29 BS H20 5.36 100 64.9 4.4 0.003 0.551 100 6.8 0.39 OH As 020 NO

PAGE 108

94 Appendix 2 c (cant i nued) 120 CH3-@-cH2CH3 CH3 C9H12 120 [ 24, M+ ], 105 [ 100, M+-CH3] 120 121 122 100 9.92 0.44 8#4 H20 3.99 100 9.3 0.148 OH A*'4 020 NO 121 @-NH2 C 8 H11N NH2 121 ( 29, M+ ], 106 [ 100, M+-CH3] 119 120 121 122 123 100 9.20 0.38 a.es H20 6.68 6.5 38.2 100 19.1 1.5 0.163 OH A*'S 020 NO

PAGE 109

95 Appendix 2 c (cent i nued) 94 @-oH CH3 C5H50 94 [ 100, H+), 66 [ 33, Cp] 94 95 96 100 6.62 0.38 6'*'4 H20 4.09. 100 7.8 0.190 OH A*'4 D20 ND 94 @-oH C5H50 NH2 94 [ 100, H+), 66 [51, Cp] 92 93 94 95 96 100 6.62 0.38 es H20 4.06 5.2 38.0 100 13.3 1.6 0.220 OH A*S D20 ND

PAGE 110

96 Appendix 2c (continued) 118 CH3-@-cH=CH2 CH3 CgH1o 11 8 [ 811 M+ L 117 [ 1 00 I M+ -H L 91 [ 30 I CH3-PH ] 115 116 117 118 119 120 100 9.98 0.44 8#4 H20 4.46 39.1 10.0 12.3 100 9.1 0.092 OH A#4 020 NO NH2 B .. 5 H20 OH A .. 5 020

PAGE 111

97 Append1 x 2 c (cant i nued) 106 0{-oH c 7 H 8 o CH3 50 CH3 108 [1001 M+ L 107 [96 I M+H 1., 91 [ 81 M+OH] 77 [ 47 1 Ph] 107 108 109 110 111 112 113 100 7.73 0.46 B H20 5. t 1 96.2 100 11.0 0.270 OH 5.27 A-4 020 60.0 100 77.1 40.4 trace 100 50.3 106 0{-oH c 7 H 8 0 CH3 NH2 109 [1001 M+ L 107 [75 I M+-H], 91 [91 M+OH] 77 [ 37 1 Ph] 107 108 109 110 111 112 113 114 100 7.73 0.46 es H20 5. t t 74.9 100 1.9 0.51 OH A-s 020 NO

PAGE 112

98 Appendix 2 -C'(cont 1 nued) CH3 B#4 H20 OH A 020 122 (Q(cH2CH3 OH CaHtoO NH2 122(38, M+ ], 107(100, M+-CH3], 77(43, Ph] 121 122 123 124 100 8.84 0.54 Bs H20 '6.33 13.7 100 16.2 0.056 OH As 020 NO

PAGE 113

99 Appendix 2 c (cant i nued) 212 CH3 C15H150 ( J CH2CH3 70 121 [ 37 I M+ ], 197 [ 1 00 I M+CH3 ], 182 [ 14 I 197 CH3 1 120 [ 15, M+92 L 91 [ 19, CH3-Ph 1 212 213 214 215 216 217 218 219 100 16.5 1.47 664 H20 14.09 100 20.4 0.103 OH 14.06 A64 020 34.1 83.2 100 8.41 49.4 22.0 0.101 100 45.2 NH2 as H20 OH As 020

PAGE 114

100 Appendix 2c (cont1nued) 206 ( C15H120 CH3 CH3 208 [ 100, M+ L 179 [15, M+271, 178 (23, M+-28] 165 [ 25, 179 -CH2 ] 205 206 207 208 209 210 100 16-.4 1.45 B#4 H20 14.40 25.9 100 17.3 0.112 OH A#4 020 trece 209 ( ;@C@ J H2N O C14H11NO NH2 209(100, M+ L 180 [27,M+-29], 104 [ 12,M+-102] 209 210 211 212 100 15.7 1.35 B#S H20 17.65 100 22.9 2.9 0.196 OH A*'S 020 NO

PAGE 115

101 Appendix 2c (continued) 212 C15H150 HO 60 CH3 212 [ 24 I M+ ], 1 07 [ 50. M+ -CH3-Ph-CH2 ] 1 05 [ 1 00 I M+ -HO-PH-CH2 ) 212 213 214 215 216 217 218 219 100 16.5 1.47 8#4 H20 14.61 100 22.0 1.7 0.797 OH 14.59 A-4 020 35.7 44.2 100 86.6 71.3 42.1 18.0 5.0 1.850 100 42.7 11.8 213 NH2-@CH2 CH2 C14H1sNO HO NH2 213 [ 8,M+ ], 106 [ 100, M+ HO-PH-CH2] 213 214 215 100 15.8 1.36 B#S H20 16.62 100 18.6 2.3 0.835 OH A*S 020 NO