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Book Review The Organic Chemistry of Aliphatic Nitrogen Compounds. (International Series of Monographs on Chemistry Vol. 28.) By B. R

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Trends and Controversies
Redox Mechanisms in Inorganic
Chemistry. (Ellis Horwood Series in
Inorganic Chemistry.) By A . G.
Lappin. Ellis H o r w o o d , Chichester,
1994. 285 pp., hardcover 5 56.50.ISBN 0-13-770751-7
This is a very timely and urgently needed book by an author who is well known
for his contributions to the understanding
of electron transfer reactions in inorganic
chemistry. The author makes it clear in
the preface that this is not a book on kinetics and mechanisms, nor on electron
transfer or the theory of electron transfer
reactions. The focus of the book is an examination of trends in mechanisms that
are found in inorganic electron transfer
reactions. And that is exactly what the
book offers, a detailed account of available literature data and the trends that can
be seen in these data.
As one would expect, the main topics
covered. following a general introductory
chapter, are the outer-sphere mechanism,
the inner-sphere mechanism, intramolecular electron transfer, and multiple electron transfer. The author has devoted an
impressive effort to compiling the available literature data and pointing out the
trends observed. The individual chapters
are excellent reviews on the topics, with
the advantage that they are all written by
the same author, resulting in a consistent
style of presentation. At the end of each
chapter a series of questions are given that
enable the reader to check the insight
gained into the topic treated. In addition,
a detailed list of references to the original
sources of the data is provided for each
The quality of production is good, except for the aspect referred to at the end of
This section contains book reviews and a list of
new books received by theeditor. Book reviews are
written by invitation from the editor. Suggestions
for books to be reviewed and for book reviewers
are uelconie. Publishers should send brochures o r
(better) books 10 Dr. Ralf Baumann. Redaktion
Angewandte Chemie. Postfach 101161. D-69451
Weinheim. Federal Republic ofGermany. Theeditor reserves the right of selecting which books will
be reviewed Uninvited books not chosen for
review will not be returned.
Aiipeii .
<‘limi. ltir. Ed. h g / . 1995, 34, No. I f
this review. Data are summarized in tables
and correlations are summarized in figures. This method of presentation avoids
excessive text and makes it easy for the
reader to find the desired data. Reaction
schemes and details of intermediate species are presented in a very clear manner,
which all adds to the convenience and
readability of the book.
The book will be of great help to anyone involved in the study of inorganic
electron transfer reactions, since it is an
up-to-date presentation of the available
literature data. Furthermore, it identifies
areas in which there is scope for further
investigation and theoretical treatment of
the data. All in all, it will be a standard
text for students and researchers involved
in the study of inorganic electron transfer
It is rather unfortunate that there are
quite a number of very obvious typing errors, especially in the first chapter of the
book. It is the responsibility of the publisher, and to some extent the author, to
eliminate such errors, which detract from
the quality of the book and fail to do justice to the author’s diligent efforts.
Notwithstanding this, the book is highly
recommended for everyone interested in
inorganic electron transfer reactions.
Rudi van Eldik
University of Erlangen-Nurnberg (FRG)
The Organic Chemistry of Aliphatic
Nitrogen Compounds. (International
Series of Monographs on Chemistry,
Vol. 28.) By B. R . Brown. C l a r e n d o n
Press, O x f o r d , 1994. 767 pp., hardcover 5 145.00.-ISBN 0-19-855783-3
The author’s aim in this well set out
work was to provide a comprehensive
survey of the organic chemistry of classical nitrogen compounds. The title is intended to indicate that heterocyclic systems are not in general covered, although
aziridines and p-lactams are in fact included. The 22 chapters deal in varying degrees of detail with the following compound types: amines (Ch. l ) , enamines
and ynamines (Ch. 2), imines, iminium
salts, ketenimines, and keteniminium salts
V C H ~ , ~ l u g . c ~ r . s P I l . \ ~thnub/H
! . 0.69451 Weinhritri, 1995
(Ch. 3 ) , nitriles, together with acyl nitriles and trimethylsilyl cyanide (Ch. 4),
N-oxides, nitrones, and nitrile oxides
(Ch. 5 ) , isonitriles (Ch. 6), cyanates, isocyanates, and their sulfur analogs (Ch. 7),
amides (especially dimethylformamide
and its acetals), thioamides, carbamates,
and sulfonamides (Ch. 8). urea derivatives and carbodiimides (Ch. 9), amidines
(Ch. lo), nitro and nitroso compounds
(Chs. 11 and 12, respectively), diazoalkanes (Ch. 13), hydroxylamines and oximes
(Ch. 14), hydrazines (Ch. 15), azo and
azoxy compounds (Ch. 16), azides
(Ch. 17), nitrates, nitrites, and nitramines
(Chs. 18 and 19), /haminoalcohols
(Ch. 20), aziridines (Ch. 21), and fl-lactams (Ch. 22).
The main emphasis is on the synthesis
of the various classes of compounds, including details of several reactions in each
case, although these are not always the
most important from a preparative standpoint. Each chapter begins with a very
brief description of the structural properties of the compounds under discussion.
Not all these introductions reflect the latest research results, and the selection of
original papers that are cited is often
idiosyncratic and sometimes incomplete.
The frequent use of the abbreviation
“F. & F.” betrays the fact that the principal literature source used was the standard work by Fieser and Fieser. Altogether there are more than 1800 literature
citations, mainly from the period 19601985. More recent citations (up to 1990)
are found only occasionally. Some important original publications by well-known
contributors to the field of nitrogen chemistry, such as Arnold, Bohme, and Viehe,
are noticeably absent. By providing better
coverage of recent reviews (including at
least references to the mow recent volumes
in the Patai series), the author could have
made it easier for the reader to gain access
to the original literature. Moreover, the
many typographical errors in authors’
names, some of which are quite grotesque,
are an annoying distraction.
The book is provided with a comprehensive subject index, but some random
tests indicate that it does not always give
the interested reader the required information. For example, the chapter on
s 22:o
enamines includes a section devoted to ten for a popular audience. But here the
I -chloro-N,N-2-trimethylpropenylamine, similarity ends.
which is correctly described as having rePeter R. Breggin, M.D., who wrote the
actions typical of a keteniminium salt; first medical books on the brain-damaghowever, this fact is not mentioned in ing effects of electroshock and psychiatric
the index, nor in the chapter on keten- drug treatment, is a leading medical critic
iminium salts. To give another example, of biological psychiatry. His efforts at rethe Vilsmeier reagent appears in the chap- form have included numerous articles and
ter on iminium salts, but its reactions are books, and U.S. media appearances on
covered in the chapter on dimethylfor- “Sixty Minutes,” “20-20”, and “Dan
mamide, with no cross-reference. Incon- Rather Reports”. His wife, Ginger Ross
sistencies of this kind make it rather diffi- Breggin, is Director for Research and Edcult to use the book. Regrettably, the ucation at her husband’s non-profit Cenauthor (who died in September 1992) was ter for the Study of Psychiatry and is his
unable to complete the manuscript him- coauthor of the forthcoming book, The
War Against Children, a critical examinaself.
I have some reservations about recom- tion of the growing psychiatric movement
mending that one should buy this book. It to increase medication of pre-school chilundoubtedly offers a clearly written and dren and minorities, with Prozac joining
well illustrated guide to a wealth of inter- Ritalin as the drug of choice. Dr. Breggin,
esting literature on nitrogen chemistry. who has been called “the conscience of
However, as it is not very up-to-date and American psychiatry”, states: “I wrote
Talking Back to Prozac because of my
because of the shortcomings mentioned
above, it can only serve as an introduction compassion for the hundreds of thousands
to the field and-with
some reserva- of people who suffer from depression, and
a reference source. As one for the many people who are being misled
would expect, it is not an alternative to the by the current emphasis on antidepresmore comprehensive standard works such sants as safe and effective treatments.” He
claims to be “one of the few psychiatric
as “Houben-Weyl” and “Patai”.
Ernst- Ulrich Wurthwein drug experts in the country without ties to
Institut fur Organische Chemie the pharmaceutical companies, and can
der Universitat Munster (FRG) therefore speak openly about Prozac.”
The Breggins’ book is an urgently needed antidote to Kramer’s book, which, they
state: “has misled hundreds of thousands
of readers and millions more who have
Talking Back to Prozac: What Doctors heard its message of better living through
Aren’t Telling You about Today’s Most chemistry.” The Breggins argue that
Controversial Drug. By P. R. Breggin Kramer “bases his theory of Prozac-inand G. R. Breggin. St. Martin’s Press, duced personality transformation on nothNew York, 1994. XIV, 273 pp., hard- ing more than a handful of his own cases,
cover $19.95.--ISBN 0-312-11486-9 . . .shows a naive reliance on the manufacturer of Prozac, Eli Lilly, in his discussion
Audiatur et altera pars! (Let the other of the drug’s impact on the brain, . . . shows
side also be heard!) In many ways this too little awareness of the pharmacologibook is the mirror image of Peter D. cal mechanisms that could cause the opKramer’s controversial best-seller Listen- posite of Prozac’s intended effect, . . .gives
ing to Prozac (Viking, 1993; for a review no credence to the Prozac survivor movement, . . . [and] sprinkles his book with
see G. B. Kauffman, American Scientist
1995, 83, 90-91). Both books were writ- moral considerations, but does not seem
ten by practicing psychiatrists; both deal to take them seriously.”
with the mechanism of operation of
In contrast to most books about psychiantidepressants, particularly the class of atric drugs, which provide the kind of inselective serotonin reuptake inhibitors formation drug advocates and pharma(SSRIs) to which Prozac, hailed by many ceutical companies want the public to
as the antidepressant drug of choice of the have, the Breggins’ book “provides infor1990s, belongs; both recount the develop- mation not readily available, even to most
ment and testing of Prozac and present experts in the field, much of it . . . systemdetailed personal case studies and ac- atically withheld from physicians and pacounts of positive and negative effects of tients alike.” Among other topics, they
the drug; both consider the ethics of ad- discuss in detail: the supposed selectivity
ministering the drug as a “mood brighten- of Prozac; the fact that Prozac was tested
er”, what Kramer himself called “cosmet- in trials of only four to six weeks before
ic psychiatry”; and both, although replete receiving U.S. Food and Drug Adminiswith extensive documentation. were writ- tration (FDA) approval; the difficulty that
VCH VerlugsgesrllschuJi mhH, 0-69451 Wemheim, 1995
Eli LiIly had in proving its efficacy during
these tests; the side effects that the FDA
failed to include in its final labeling requirements; Prozac’s short-term and longterm impacts on the brain; how Prozac
acts as a stimulant similar to the addictive
drugs cocaine and amphetamines; the
economic and political forces (“the medical-industrial complex”) backing promotion of the drug; the dangers of possible
Prozac addiction, abuse, and withdrawal
symptoms; the seriousness and frequency
of Prozac’s side effects; the growing evidence from case study after case study
that Prozac can cause violence and suicide; the avalanche of lawsuits against Eli
Lilly involving Prozac; and the social and
workplace implications of using drugs,
not to cure depression, but to change personality and enhance performance.
The authors also disclose the intricate
web of cozy connections between the
FDA, the drug companies, and the psychiatric community (what they call the
“psycho-pharmaceutical complex”); the
close ties that existed between Eli Lilly
and both former U.S. President George
Bush and former U.S. Vice-president Dan
Quayle; and the FDA ban on the food
supplement L-tryptophan, which forces
people to use SSRIs instead. They decry
the flooding of the country with propaganda in favor of taking drugs-“a technological shortcut for people who want to
find their real personalities the fast-food
way”-for conditions such as depression,
which, in many cases, may be part of the
human condition and a normal concomitant of an empathic life. They explore the
positive side of depression and state: “To
the degree that a human being is capable
of suffering deeply, to that same degree
the human being is capable of a full, rich,
exciting, and creative life.” They describe
the resounding success achieved by more
humane non-drug alternatives to the “National Prescription Drug” for the treatment of depression. In their copious notes
the Breggins provide an extensive bibliography listing every author, article, or project mentioned in the book, and in the
appendix they give useful information
about the Psychiatric Reform Movement
and the Prozac Survivors Support Group,
including addresses and telephone numbers. They also provide a form and full
directions for filing an adverse drug reaction report with the FDA.
This fact-packed book is a gold mine of
valuable data for practicing scientists, science educators, pychiatrists, historians of
science, policy makers, and those concerned with the relations between government regulatory agencies and pharmaceutical companies. On a more personal level,
0570-0833/95/lllt-l250 $10.00+ ,2510
Angew Chem. I n f . Ed. Engl. 1995, 34, N o . 11
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international, chemistry, book, series, compounds, organiz, aliphatic, nitrogen, vol, review, monograph
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