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Book Review Synthetic Organic Photochemistry. Edited by W. M. Horspool

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The book consists of three chapters: introduction,
anodic oxidations and cathodic reductions. These are followed by a short appendix in which it is demonstrated that
the reactions can be carried out with very moderate apparatus.
In the introduction he discusses the principle and potential of redox Umpolung, unfortunately rather scantily. This
is followed by a consideration of the consequences of the
heterogeneous character of the reaction upon the stereochemistry of the conversion and upon the concentration
relationships of the active species that are generated. The
influence of the choice of electrode material and electrolyte on product distribution are missing here. The effect of
the electrochemical procedure on the stereochemical
course of a reaction could easily be overestimated through
the presentation of three particularly impressive examples.
Anodic oxidation, with 120 pages, occupies two thirds of
the book. This chapter is organized according to the structure of the substrates. Whether this arrangement is more
accomodating to a synthetic chemist than organization by
reaction type is to be left undecided. Yet, having chosen
this system, it would have been more sensible to use it for
the reductions too. The section on amine oxidation is, in
spite of its great synthetic significance, clearly over-represented with 25 pages.
The chapter on cathodic reductions seems to be rather
too brief with 35 pages only. It is organized by reaction
type. Even if it is admitted that at present oxidation reactions show a somewhat greater synthetic potential, this abbreviated presentation of synthetic possibilities at the cathode does not meet ones expectations. For example, there
is no room for the versatile cathodic heterocycle syntheses
and conversions.
It is taken for granted that the author should give preference to his own work in the choice of examples; however,
there are some places where a rather more balanced presentation would have been preferred. To meet the claims of
the book to present organic electrochemistry as a synthetic
tool, it would have to emphasize more strongly the principal synthetic possibilities at the beginning of each section
and perhaps compare these with the chemical alternatives.
That would offer welcome orientation to the chemist engaged in synthesis. Unfortunately, the index cannot supply
this help since it lists, essentially, only compounds, classes
of compounds o r technical terms and does not link compound and methods or vice-versa. Unfortunately, it is incomplete.
In spite of these reservations, the book should provide
valuable and stimulating reading for all synthetically
oriented chemists. This presentation of organic electrochemistry as a synthetic tool should be a suitable way to
dispel inhibitions about this technique. It can only be
hoped that no potential reader will be deterred by the relatively high price.
Eberhard Steckhan [NB 705 IE]
Institut fur Organische Chemie und Biochemie
der Universitat Bonn (FRG)
Synthetic Organic Photochemistry. Edited by M’. M . Horspool, Plenum Press, New York 1984. xvii, 534 pp., hardback, $ 75.00.--ISBN 0-306-41449-X
The renaissance of synthesis in organic chemistry has
also had a stimulating influence on photochemistry. This
Angew. Cliem. Inr. Ed. Engl. 25 11986) No. 4
welcome development cannot, however, disguise the fact
that photochemical reactions still play only a minor rdle in
organic synthesis. One reason for this surely lies in the inadequate communication between those engaged in synthesis and those investigating mechanisms.
Up to now, only a few have mastered the interdisciplinary transfer of results from physical chemistry to modern
synthesis; thus, any attempt to make the synthetic potential of photochemistry accessible to a wider circle is very
much to be welcomed. However, the question ought to be
raised whether the prefix “Synthetic” suffices to differentiate this book from a well known series, of which six volumes have already appeared. As the foreword trenchantly
comments, the selection of material in any single volume
work is bound to be incomplete. If, on this account, however, particular stress has been laid on topicality and synthetic potential, then why are such significant classes of
compounds as cyclohexadienones and di-n-methane systems not covered, while topical problems like chirality
transfer in cycloadditions are treated comparatively briefly
and incompletely? The list of such examples could be continued.
The book does, of course, contain useful informationin some cases very much so-on the photoreactions of arenes, enones, phthalimides, azirines, benzothiophenes and
furans and indoles. The same applies for the Paterno-Buchi reaction, for electron transfer reactions in particular,
and for photochemical methods with protecting groups.
The final chapter, on experimental techniques, does indeed offer an introduction, but this is not exhaustive. Here,
every reader is strongly recommended to refer back to textbooks o r to “Houben-Weyl”.
Around half the topics presented here have already been
extensively described elsewhere in surveys, e.g. in the series referred to above. Since most of these contributions
have been written from a synthetic standpoint and thus
cite similar examples and, moreover, provide more mechanistic information, the editor of this book could easily
have avoided repetition and thereby made room for other
items. In summary, it can be said that this book provides
an introduction to the subject. The reader should, however,
have prompt recourse to other books on this topic.
Jochen Mattay [ N B 71 1 IE]
Institut fur Organische Chemie der
Technischen Hochschule Aachen (FRG)
Techniques in Organic Reaction Kinetics. By P. Zuman and
R . C. Patel. John Wiley, Chichester 1984. 340 pp., hardback, L 57.25.--ISBN 0-471-103556-4
This book is based on lectures given by the authors. In
four chapters it gives an easily readable insight into the
kinetic methods of physical organic chemistry. The theory
of chemical reaction kinetics is only brought in to the extent required for the measurement of reaction rates. After a
short introduction, the physico-chemical methods of measuring the rates of slow reactions are dealt with in chapter 2
(40 pages). Chapter 3 (201 pages) is concerned with the
analysis of kinetic data. It is consciously modelled on the
book by Frost and Pearson (A. A. Frost, R. G. Pearson:
Kinetics and Mechanism). It contains formal kinetics with
many examples from organic chemistry; the influence of
ionic strength, solvent characteristics and substituent effects are discussed in depth. Chapter 4 (82 pages) handles
the study of fast reactions; it follows E. F. Caldin’s book
38 1
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