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Book Review Non-Benzenoid Conjugated Carbocyclic Compounds. By D. Lloyd

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Because of the professional activities of the author, the
emphasis of the book is on the chapters concerned with the
application of hydrazine as a rocket propellant. A new
technology has been developed here that is rarely reviewed
in the normal chemical literature. Who, for example, is
aware that the anhydrous hydrazine employed for the Viking landing o n Mars had to be freed from organic impurities by fractional crystallization because of apprehensions
that hydrazine cyanide, occurring in the exhaust gases,
might interfere with the biological experiments?
In the important section on the toxic properties of hydrazine and its compounds the author points out that investigations are still in progress and that there is no lack of
contradictory results.
The reviewer has several reservations in spite of the
many positive aspects of this book. For instance, the almost 60 lines per page and the relatively small type make
reading difficult. However, the following objections are of
more importance: Today, three processes are employed for
the production of hydrazine on an industrial scale,
whereas one process was formerly employed, the urea
process. Each of these processes are, of course, described
(flow diagrams are also provided) but one also finds a host
of irrelevant details from the patent literature. Some statements are even incorrect. In the Bayer process their is no
hydrazine formed which is intercepted as the ketazine.
Diaziridine is a feature of the (not practised) Bergbau
process and not of the Bayer process. Since these processes
are to be found under the heading “Bergbau-Bayer-Whiffen Process” this section can only confuse readers who are
unfamiliar with the matter. It is also questionable if a ketone imine is a n intermediate in the PCUK process.
In the discussion of the large number of processes that
are not employed for the synthesis of hydrazine on an industrial scale, e.g. the fixation of nitrogen in complexes
with subsequent reduction or electrochemical methods,
one misses a short account as to why these interesting variants are not employed industrially. The description of the
application of hydrazine in fuel cells is a positive example
where it is clearly stated that technical application is not to
be expected (and why).
In all, a necessary book for all who have anything to d o
with hydrazine; but care must be taken by those searching
in the chemistry part of the book for rapid u p todate information concerning the present state of the art in this
field.
Reinhard Schliebs [NB 668 IE]
Bayer AG, LeverkusenBayerwerk (FRG)
Details of the preparation of the non-commercially available substances would have been desirable here.
The following chapters describe, according to reaction
type, a wide range of natural product syntheses with selenium reagents. In the second chapter entitled “Seleniummediated oxygenations” the reader finds alongside allylic
oxidation with selenium dioxide also examples of the
modern variations of this well-known reaction which have
been introduced especially by Sharpless and Barton. In
Chapters 3 a n d 4, which deal with dehydrogenations, asomewhat arbitrary-distinction is made between “Selenium-mediated Dehydrogenations” ( = Dehydrogenations
without the isolation of a n intermediate) and “Organoselenium-mediated Olefinations”. By this the authors understand the synthesis of olefins by the preparation of selenium oxides followed by elimination, a method which has
become known under the names of Sharpless and Reich.
Chapter 5 briefly covers reductions with selenium reagents. Chapter 6 is concerned with selenium-stabilized carbanions which were first described by Seebach at the end
of the 1960s and have since found extensive application by
Krief and Reich. Unfortunately the expression “synthetic
equivalent” is employed in the review at the commencement of the chapter when “synthon” was what was meant.
The electrophilic addition of selenium reagents to C C double bonds and their subsequent cyclization by intramolecular reaction of the selenium ion (e.g. “selonlactonization”)
is described in the seventh chapter with many examples
including some from Nicolaou himself. Finally, a potpourri
of reactions, some of which have not (yet) been employed
in natural product synthesis, is included under the title
“Miscellaneous Applications of Selenium Compounds”.
Before going into the numerous examples of applications, the key reactions are presented in generalized form
in the individual chapters by means of clear formula
graphics. The target molecules range from terpenes via steroids and alkaloids to prostaglandins and macrolides. In
accordance with the intensions of the book only the relevant steps of multistep syntheses are reported. Unfortunately the yields of the individual steps are not always included in the clearly presented reaction schemes.
The authors have been able to provide a comprehensive
insight into the potential of selenium reagents which is,
nevertheless, understandable even to the advanced student. A successful book in spite of the flaws mentioned.
Manfred Braun [NB 675 IE]
Institut fur Organische
Chemie I der Universitat
Dusseldorf (FRG)
Selenium in Natural Products Synthesis. By K . C. Nicolaou
and N . A . Petasis. CIS Inc., Philadelphia 1984, 300 pp.,
bound, $ 39.50.--ISBN 0-914891-00-6
It is well-known that the usefulness of novel synthetic
methods depends on their application to the synthesis of
complex natural products. In the last 15 years the efforts of
several groups with organoselenium compounds have led
to the development of many preparative methods. This
book documents the fact that these have found frequent
use up till now in the synthesis of natural products and
evaluates this, rightly, as evidence for the breadth of application of selenium chemistry.
The introductory chapter reports very briefly on the particularities of organoselenium compounds; then the most
important reagents are listed in tabular form, together with
the comment that many are now commercially available.
Non-Benzenoid Conjugated Carbocyclic Compounds. By D.
Lloyd. Elsevier, Amsterdam 1984. xvi, 431 pp., bound,
HFI. 260.00- ISBN 0-444-42346-X
This book communicates a feeling of the fascination
which has brought synthetic chemists, spectroscopists and
theoreticians together in a unique manner. The chemistry
of non-benzenoid conjugated carbocycles has years of hectic development behind it; this is reason enough for the
stock-taking that Lloyd planned. The author has also succeeded in representing the continuous, the living force of
his subject which transcends the ups and downs of fashion,
particularly by the inclusion of original work u p to 1983.
The concept of aromaticity and its unchanging importance is dealt with in a n introductory chapter. This section
impresses with its historical completeness; it has a strongly
narrative character, but suffers from the absence of a dis-
Anyeu.
Chem.
Iiir.
Ed. Engl. 24 119851 No. I 1
1007
cussion of, for instance, the theory of the fixation of double bonds. The following chapters are devoted to cyclopentadienes and cyclopentadienide ions (2.), cycloheptatrienes and tropylium ions (3.), cyclopropenes and cyclopropenium ions (4.), cyclobutadienes (5.), cyclooctatetraenes and cyclononatetraenes (6.), annulenes (7.), and bicyclic and polycyclic compounds (8.). The descriptions of
the results are always comprehensive: thus, in the case of
the seven-membered ring compounds, the coverage ranges
from tropylium ions to tropones, tropolones, heptafulvenes
up as far as the cycloheptatrienylidenes and cycloheptatrienide ions. The description of the individual substance
types is always under the headings “Synthesis”, “Spectra
and Structure” and “Chemical Reactions”.
The book is convincing in the care and specialist knowledge with which the relevant literature has been collected
and pithily reviewed. The sympathetic “devotion to the literature” which is the real strength of the book becomes an
unintentional disadvantage in instances were a criticism of
the original work or a discussion of discrepant results is
called for. The text also remains a little conventional because the beginnings of newer developments within the
chemistry of conjugated carbocycles such as, for example,
“aromaticity and electrical conductivity” or “multilayered
TI systems and properties of stacks” remain unmentioned.
Taking this into account it remains a resumee which will
be of great value to every interested chemist who makes
use of the material collected in it.
The publishers must be excluded from the recognition
awarded to the author. The author deserved better support
in the large quantities of graphics. The print and graphics
have an improvised appearance and are at great variance
with the exaggerated price.
Klaus Miillen [NB 669 IE]
Institut fur Organische Chemie der Universitat
Mainz (FRG)
Reactive Intermediates. A Serial Publication. Vol. 3. By M .
Jones, Jr. and R . A . Moss. John Wiley, Chichester 1985.
ix, 435 pp., bound, X 96.00.-ISBN 0-471-01893-7
Encyclopedia of Polymer Science and Engineering. 2nd Edition. Vol. I: A-Amorphous Polymers. Edited by H . F.
Mark, N . M . Bikales, C. G . Overberger, G . Merzges, and
J. I . Kroschwitz. John Wiley, Chichester 1985. Ixii, 843
pp., bound, subscription price: X 175.00, individual volume: L‘ 210.00.-ISBN 0-471-89540-7; 19 further volumes, a supplement, and an index volume are scheduled
to appear before June 1989.
Laborbucher Chemie. Praxis der Hochleistungs-Flussigkeitschromatographie. 3rd Edition. By V. Meyer. Diesterweg Salle Sauerlander, Frankfurt 1985. x, 245 pp., paperback, DM 54.00.--ISBN 3-425-05452-X
Analytical Measurement and Information. Advances in the
Information Theoretic Approach to Chemical Analyses.
By K . Eckschlager and V. Stepanek. Research Studies
Press, Letchworth (Herthfordshire, England) 1985. xii,
140 pp., bound, f 25.00.-lSBN 0-86380-021-1
IUPAC Chemical Data Series No. 31. Chlorine. International Thermodynamic Tables of the Fluid State-8. Tentative Tables. By S. Angus, B. Armstrong, and K . M . d e
Reuck. Pergamon Press, Oxford 1985. xviii, 162 pp.,
bound, f 30.00.--ISBN 0-08-030713-2
Wissenschaftliche Taschenbucher WTB Biologie. Molekulare Wirkungsmechanismen von Pharmaka. Eine Einfuhrung in die Molekularpharmakologie. By P. Nuhn and
H.-J. Hofmann. Akademie-Verlag, Berlin 1985. 188 pp.,
paperback, DM 16.00.-Order-No. 763-312-0 (7294)
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Handbook of Chemical Equilibria in Analytical Chemistry. By S. Kotrly and L. Sucha. Ellis Horwood, Chichester 1985. 414 pp., bound, f 45.00-ISBN 0-85312-107-9
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Special Publication No. 52. Recent Advances in the Chemistry of fJ-Lactam Antibiotics. Third International Symposium, Cambridge (England) 2-4 July 1984. Edited by A .
G. Brown and S . M . Roberts. The Royal Society of
Chemistry, London 1985. viii, 391 pp., paperback,
X 26.50.-ISBN 0-85186-955-6
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