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Book Review Electroorganic Syntheses Part I Oxidations. By S

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editors and publisher have put together a high-quality reference which will find almost daily use among those involved in biochemistry, biology, chemistry and related areas. This series is strongly recommended to libraries and
groups where analyses are routinely done.
Philip 13. Stein and George M . Whitesides [NB 726 IE]
Department of Chemistry, Harvard University
Cambridge, MA 02138 (USA)
Electroorganic Syntheses, Part I: Oxidations. By S . Torii.
VCH Verlagsgesellschaft, Weinheim 1985. xi, 338 pp.,
bound, DM 138.00.--ISBN 3-527-26318-7
Shortly after the publication of Shono’s book, S . Torii,
another important electroorganic chemist engaged in synthesis, has addressed the subject in a monograph. The first
volume of this work has been published; the second part
(on reductions) is planned. This volumed is based on a
monograph of the author’s, which appeared in 1981 in Japanese. It amounts to more than a simple translation into
English, however, since it has been revised and extended.
Literature references cover publications up to 1983; in a
few cases there are even references from 1984. Since the
author is not aiming at an exhaustive presentation of organic electrochemistry, literature from earlier than 1970 is
considered only in a few cases.
This book, similarly to Shono’s, is directed at chemists
engaged in synthesis, i.e., in the first place, at non-electrochemists. It is arranged in thirteen chapters, of which the
first, “Electrooxidation and Product Selectivity”, clearly
gives the intention of the whole work from the outset.
Chapters 2-10 and 12 deal with the electrooxidation of
particular classes of compounds. Two chapters are concerned with catalytic phenomena which have achieved
more and more significance lately: indirect electrooxidation and the use of electrochemically generated acids.
In these chapters, the author presents an abundance of
synthetically interesting reactions, clearly arranged. Nonelectrochemists are not put off by a lengthy explanation of
the theoretical basis or exhaustive presentation of reaction
mechanisms. Instead, the emphasis is placed on the discussion of selectivity and the steering of reactions. The author
points out that high selectivity in the reactions can only be
achieved through the right choice of the reaction parameters, especially of solvent, conducting salt and electrode
material. Particularly in the first chapter, but also in all
subsequent parts of the book, the influence of these parameters on the course of the reaction i s repeatedly discussed in detail and possibilities for steering the reactions
are worked out. Since this is done, to a large extent, on an
empirical basis, it will appeal to synthetic chemists. It must
be said, however, that this approach may perhaps distract
those readers who want only to cast a quick glance at the
synthetic potential of the method.
As the author points out in the foreword, he is attempting to present results in a form which makes plain the possibilities for their application in synthesis. An appendix to
Chapter 1 contributes particularly to this end. Here, the
possible conversions are set out schematically, arranged
according to the kind of bond formation, bond splitting,
rearrangement and functionalization, and linked with the
appropriate reaction conditions and with references to
pages and chapters of the book. Such a presentation is especially valuable, if information is required on a particular
type of conversion. Synthetic chemists would surely, how484
ever, have welcomed a critical comparison of the pros and
cons of electrochemical methods against current chemical
alternatives. It would have been helpful for the evaluation
of the potential of electroorganic synthesis by non-electrochemists had the author expounded the principle of redoxUrnpolung, which underlies electrochemical reactions.
It is annoying, however, that in an otherwise very carefully edited book, the literature references in Chapter 1,
contain some monographs in Japanese or translations into
Japanese, while the English originals or equivalent works
in English are not cited. Unfortunately, as frequently encountered, the index has not been given much attention.
Not only is it incomplete, but it also suffers from the fact
that the entries, mostly compounds, are not further qualified, so that their relationship to a method, type of conversion, or property is not established. This applies, for example, to the entry “anisaldehyde” in the index. If the reader
were to be properly guided, the qualification “from methoxytoluene” would be necessary. As it is, the page number given refers only to the indirect electrochemical preparation, while the direct electrochemical synthesis, spanning
almost two pages in Chapter 3, is not mentioned.
It is to be welcomed that, with these books by Shono and
Torii, there are now two monographs available on the subject of electroorganic synthesis that are directly aimed at
synthetic chemists. In both cases, it is not so much the electrochemical method itself which is given prominance to,
but rather the great synthetic potential of this method,
which is still underestimated. The books are written in a
style which makes this fascinating area accessible to every
reader. Thus, it is to be hoped that both books will achieve
the largest possible circulation amongst synthetically
oriented chemists. The length of the two books, in one case
17 1 pages and, in the other, 338 pages for volume 1 alone,
shows quite clearly that the intended readership is different for each. Shono’s monograph is especially suitable for
those who want a brief survey of the manifold possibilities
of electrosynthesis, who want to kindle an interest or who
are looking for new synthetic concepts. Students majoring
in chemistry should belong to this group, if they are not
put off by the relatively high price. On account of its
strong emphasis on selectivity and the steering of electrochemical reactions, Torii’s book is not only suitable as a
source of general information, but also offers a lot of concrete suggestions as to the most favorable procedure and
the most suitable reaction conditions to those who want to
incorporate electrochemical steps into their synthetic
plans. It presents to the interested reader a good survey of
the present state of the art and makes it clear that the high
expectations on selectivity of modern synthetic operations
can be fulfilled by electrosynthesis. It is, therefore, a book
that can convince the synthetic chemist of the advantages
of organic electrochemistry so that he will refer to it again
and again.
Eberhard Steckhan [NB 705 a IE]
Institut fur Organische Chemie und Biochemie
der Universitat Bonn (FRG)
Structure and Spectra of Molecules. By W. G . Richards and
P. R . Scott. John Wiley, Chichester 1985. ix, 172 pp., paperback, L 6.95.--ISBN 0-471-90575-0
In this brief introduction, the authors are principally
concerned with illustrating the physical relationships of
spectroscopic quantities with the electronic and geometric
Angew. Chem. I n t . Ed. Engl 25 (1986) No. 5
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