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Book Review Organoselenium Chemistry I. Functional Group Transformations. By A. Krief and L. Hevesi

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BOOK R E V I E W S
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Organoselenium Chemistry I. Functional Group Transformations. By A . Krief and L. Hevesi. Springer, Berlin
1988. xi, 221 pp., hardback, DM 186.00.-ISBN 3-54018629-8
Selenium, whose discovery is ascribed to Berzelius in
1817, was during the 19th century already being mentioned
occasionally in reports of organic compounds and organic
reactions. It moved into the limelight of organic synthesis
in the early thirties of the present century, with the discovery by H . L. Riley that a-CH, groups in olefins and ketones can be oxidized using selenium dioxide. At about the
same time 0. Diels, L. Ruzicka and others observed the
dehydrogenating effect of elemental selenium, which at
that time was used especially for converting steroids to
phenanthrene derivatives or chrysene. The mid-seventies
saw the beginning of a blossoming of organoselenium
chemistry which continues today. On the one hand more
and more organic molecules possessing selenium-containing skeletons or functional groups became accessible, while
on the other hand various selenium reagents for carrying
out especially mild or highly specific transformations were
discovered. This work is associated particuIarly with the
names of N . D . Jones and K . B. Sharpless.
The present-day importance of organoselenium chemistry has naturally led to the publication of numerous reviews and monographs on selenium compounds, and to
these is now being added the work by Krief and Hevesi,
which is to consist of two volumes. The authors’ aim is to
give an account of the most common selenium reagents,
and the breadth and limits of their usefulness in organic
synthesis.
The first volume, published in 1988, deals with actually
or formally possible single stage processes involving selenium-containing intermediates, which cannot or need not
be isolated. The second volume will treat processes with
two or more stages involving selenium-containing intermediates. In addition there is to be a section on the preparation of the most important selenium reagents.
The introduction to Volume I deals with the occurrence
of selenium and its compounds in nature, and with toxicity, biochemical functions, and some industrial and ecological aspects. This is followed by ten chapters on selenium
compounds in organic synthesis, arranged according to the
Angew. Chem. I n l . Ed. Engl. 28 (1989) No. 2
different oxidation states of selenium (- 2 to
6). The
contents of the individual chapters are best summarized by
listing the chapter headings: Reactions involving hydrogen
selenide, selenols and related compounds; Reactions of
metallic or amorphous selenium with organic molecules;
Reactions involving selenium oxides and their derivatives;
Reactions using selenenyl halides and related compounds;
Reactions involving benzeneseleninic anhydride and related compounds; Reactions using benzeneseleninyl halides ; Reactions using perseleninic acids; Selenium dioxide
oxidations; Reactions of imidoselenium compounds ;
Reactions involving selenium oxychloride and selenium tetrahalides.
As well as the synthetic methods themselves, the mechanistic aspects necessary for understanding them are
briefly covered. The style of the book combines fluency
and brevity with a high information content; the clearly
presented reaction schemes and a comprehensive keyword index are especially good features. However, in the
descriptions of the syntheses one often feels the lack of a
critical evaluation, and especially of comparisons with
other known methods for carrying out the same transformations. The book is definitely not a substitute for a comprehensive review of organoselenium chemistry, such as is
contained in the two volumes on selenium and tellurium
compounds published in 1986 and 1987 in the series “The
Chemistry of Functional Groups (editors S . Patai and 2.
Rappoport), but it will nevertheless be a valuable aid to the
preparative chemist, and especially to the natural products
chemist.
Herbert Meier [NB 933 IE]
Institut fur Organische Chemie
der Universitat Mainz (FRG)
Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis. Novel Strategies in Synthesis. By K . B. G . Torssell.
VCH Verlagsgesellschaft, Weinheim/VCH Publishers,
New York 1988. xii, 332 pp., hardback, DM 115.00.ISBN 3-527-26641-O/O-89573-304-8
The second volume in the series “Organic Nitro Chemistry” treats some further functional N - 0 derivatives such as
nitrile oxides, nitrones and alkyl and silyl nitronates with
the isoxazoles derived from them and their hydrogenated
forms. The synthesis, reactivities and applications of the
compounds are described.
After an introductory discussion of general aspects
(Chapter 1, pp. 1-47: dipolar character, 1,3-dipolar addition, physico-chemical properties of the isoxazoles, stereoand regiochemical considerations, asymmetric induction),
the first part of the book (Chapters 2 and 3, pp. 55-89)
deals with the synthesis and chemistry of nitrile oxides and
nitrones. Since there are already several excellent review
articles covering this field, a condensed survey is given
here. (However, for the nitrile oxides there is no mention
of the elegant synthesis from nitromethyl derivatives and
Ph3P-CC14 reported in 1983 by Furukawa, Hashimoto and
Nishiko). Next comes a review (Chapter 4, pp. 95-122) of
the synthesis, properties and reactions of alkyl and silyl nitronates, which are of interest as reagents in the nitro-aldol
reaction (Henry reaction) as well as 1,3-dipoles.
The largest part of the book is Chapter 5 (pp. 129-270),
which is concerned with the use of nitrile oxides, nitrones
227
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