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Book Review Ozonation in Organic Chemistry. Vol. 1 Olefinic Compounds. By P. S. Bailey

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Ozonation in Organic Chemistry. Vol. 1 : Olefinic Compounds.
By P. S. Bailey. Academic Press, New York 1978. xiv, 272
pp., bound, E 18.50.
Many summaries have appeared on the ozonolysis of
alkenes, but up to now there has been no authoritative representation and discussion of the current state of affairs. The
present monograph fills this gap. It is a fitting tribute to
Rudolf Criegee, “a true gentleman, a dedicated scientist and
teacher”; the author received the decisive stimulus for his
scientific work in the Karlsruhe Laboratory.
Unlike “Organic Syntheses”, the book is not a collection
of recipes intended for hurried searchers; it is rather a conscientious account of a slice of chemical history. Ozonolysis is
a prime example of the way in which mechanistic thinking
acts as a stimulus to new experiments. The reviewer feels
that the central part of the book consists of Chapters VI
and VII, which describe the dramatic development in the
determination of the mechanism of ozonolysis over the last
15 years.
Ozonides are formed by 1,3-dipolar cycloaddition, followed
by a 1,3-dipolar cycloreversion of the primary ozonide and
a renewed 1,3-dipolar cycloaddition of the carbonyl oxide
to the carbonyl bond. If the carbonyl oxide had been generally
recognized as a 1,3-dipole, the analogy with nitrones would
have ailowed the syn,unti isomerism to have been foreseen
and have saved some false trails; the alternative mechanisms
proposed by Story and Murray have not stood up to testing.
Criegee himself lived to see the reinstatement of his mechanism
of ozonolysis, and contributed to it with some brilliant experiments.
Much effort is still being devoted to the question of how
the structure and the reaction conditions affect the &,trans
ratio of ozonides.
Advances in the oxidation and reduction of ozonides over ’
the last two decades are also reported in detail (Chapter
VIII), as are the numerous types of anomalous ozonolysis
reactions (Chapter IX). The competition between ozonide formation and epoxidation (Chapter XI) can now be regarded
as well understood, while gas phase ozonation (Chapter XII)
is still very unclear in its mechanism and, because of the
low yields, is also unattractive.
The literature (717 references) has been covered until the ’
end of 1976. This volume is to be followed by a second,
which will deal with the ozonation of alkynes, arenes, and
heterocyclics, and with the reactions of ozone with nucleophilic
agents and the C H bond. This first volume, in itself, deserves
wide circulation.
R o y Huisgen [NB 464 IE]
Rryisrerrd names. trodemorks.
0
PIC.
Molecular Movements and Chemical Reactivity as Conditioned
by Membranes, Enzymes, and Other Macromolecules. XVIth
Solvay Conference on Chemistry, Brussels, November 22November 26, 1976. Edited by R. Lefever and A. Goldbeter.
John Wiley & Sons, London 1978. xiii, 346 pp., bound,
E 25.50.--ISBN 0-471-03541-6
Terpenoids and Steroids, Vol. 8. Senior Reporter: J . R. Hanson.
The Chemical Society, London 1978. ix, 301 pp., bound,
DM 115.00-ISBN 0-85186-326-4.-A volume in the series
“Specialist Periodical Reports”
Luminescence Spectroscopy. Edited by M . D. Lumb. Academic
Press, London 1978. ix, 375 pp., bound, E 24.00-ISBN
0-12-459550-2
Electron Spectroscopy: Theory, Techniques, and Applications,
Vol. 2. Edited by C. R. Brundle and A. D. Baker. Academic
Press, New York 1978. xi, 287 pp., bound, $ 36.25.-ISBN
0-12-137802-0
Ubungsbuch Hohere Festigkeitslehre. Elastizitatstheorie, Plastizitatstheorie, Viskoelastizitatstheorie.By H. Goldner. Physik-Verlag, Weinheim 1978. 367 pp., bound, DM 28.00.ISBN 3-87664-037-7
Erratum
Due to an unfortunate printing error in the communication:
Synthesis of Thymosin czl, a Polypeptide of the Thymus by
Ch. Birr and U . Stollenwerk, Angew. Chem. Int. Ed. Engl. 18,
394 (1979), the yield given in reference [4b] fS.-S. Wang et al.)
should read 9.2 %.
used in this ,ournul, e v m without specific indicariun thweqf, are tiof 10 he considered uiiproteclrd b y lor,
Verlag Chemie. GmbH, D-6940 Weinheim, 1979.
~
Printed in West Germany by Zechnersche Buchdruckerei, SpeyerIRhein.
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~
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Editor: 0.Smrekar . Translation Editors: A . J . Rackrtrau. and A Stiniwn
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492
Angew. Chrm. Int. Ed. Engl. 18 (1979) No. 6
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