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Book Review Reactive Intermediates. Volumes 1 and 2. Edited by R. A. Abramovitch

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10
11
CAS Regsitry numbers:
3, 85371-18-2; 4, 85371-19-3; 5, 52385-60-1; 6a, 23691-13-6; 6b, 85371-20-6;
7a, 85371-21-7: 7b, 85371-22-8; 8a, 85371-23-9; 8b, 85371-24-0; 9a, 8537125-1 ; 9b, 85371-26-2; 10, 3433-80-5; 13, 85371-27-3; acrolein, 107-02-8.
[I] a) B. Lythgoe in R. H. Manske: The Alkaloids. Vol. X, Academic Press,
New York 1968, p. 597; b) K. Nakanishi, T. Goto, S. Ito, S. Natori, S .
Nozoe: Natural Products Chemistry, Vol. I , Kodansha-Academic Press,
Tokyo, Japan 1974, pp. 281-284; c) R. W. Miller, J . Nut. Prod. 43
(1980) 425.
S.
Kende, M. Benechie, D. P. Curran, P. Fludzinski, Tetrubedron Lett.
1979,4513; B. M. Trost, H. Hiemstra, J. Am. Chem. SOL.I04 (1982) 886;
S. F. Martin, I. B. White, R. Wagner, J . Org. Chem. 47 (1982) 3192.
191 a) The alcohol 5 is obtained by reduction of the corresponding diene ester with diisobutylaluminum hydride (I. Alkonyi, D. Szabo, Chem. Ber.
100 (1967) 2773) (90%) or by ene reaction of tetramethylallene and formaldehyde (R. C. Blurne, US-Pat. 3806511 (1974). and 3880669 (1975),
Du Pont; Chem. Abstr. 81 (1975) 3344 and 82 (1975) 172295).
[ 141 F. W. Wehrli, T. Wirthlin: lnterpretation of Carbon-13 NMR-Spectra,
Heyden, London 1978, p. 22.
[ S ] For recent synthetic efforts related to the taxane problem see: A.
attributable to the sp3-bridgehead C atom: the 14.4 ppm
shift downfield relative to cycloadduct 3 is consistent with
the 0-effect produced by gem-dimethyl substituents at C151’41,confirming the regiospecificity of the cycloaddition.
Received: January 12, 1983 [Z 239 IE]
German version: Angew. Chem. 95 (1983) 422
The complete version of this manuscript appears in:
Angew. Chem. Suppl. 1983, 564-570
BOOK REVIEWS
Reactive Intermediates. Volumes 1 and 2. Edited by R. A.
Abramouitch. Plenum Press, New York 1980 and 1982.
xiii, 522 pp., bound, $ 49.50 and xv, 599 pp., bound,
$ 59.50.
It is intended that the series “Reactive Intermediates”
shall provide articles concerning relatively new areas of
reactive intermediate chemistry, at irregular intervals. In
this it complements another series, also entitled “Reactive
Intermediates” (edited by M . Jones Jr. and R. A. Moss, so
far two volumes), which reports mainly on advances in
well-known intermediates (carbanions, carbonium ions, radicals, carbenes and nitrenes).
The first volume contains contributions on: the preparation and reactions of atomic carbon (P. B. Sheulzn, 36 pp.,
the dependence of the products formed on the mode of
generation of the atomic carbon is exhaustively discussed);
metal atoms as reactive intermediates (K. J. Klabunde, 1 1 2
pp., deals with experimental techniques, including commercial apparatus, as well as applications in organometallic synthesis and in matrix isolation spectroscopy); aminium radicals (Y. L. Chow, 112 pp., surveys chemical, photochemical and electrochemical amine oxidations and the
homolysis of N-chloramines and N-nitrosamines); arylcarbenes in the gas phase (C. Wentrup, 56 pp., discusses automerizations and ring contractions that the author has investigated by isotopic labeling); and metal salt-catalyzed
carbenoids (D.S . Wulfman and B. Poling, 191 pp., give a
detailed account of the carbenoid concept and the mechanism of methylene transfer together with numerous references to preparative applications of metal salt-catalyzed
reactions of diazoalkanes).
Volume 2 contains contributions on: arylnitrenes in solution (E. F. V. Scriuen, 54 pp., with emphasis on the singlet-triplet problem and the reaction route to azepines); nitrile ylides and nitrenes from 2H-azirines (A. Padwa and P.
H . J. Carlsen, 64 pp., Huisgens’ work on the cycloadditions
of nitrile ylides is appraised and photochemical and intra420
molecular variants are discussed); radical cyclization by
intramolecular addition (J.-M. Surzur, 174 pp., the influence of substituents, chain length, and heteroatoms on
the cyclization of unsaturated radicals is treated in a
clearly set-out arrangement of the extensive material.
Alongside the kinetic and stereochemical aspects, attention
is particularly paid to the synthesis of bicyclic and polycyclic compounds); and the reactions of silicon atoms and
silylenes (Y.-N. Tang, 70 pp., insertion and addition reactions have analogies with and show differences from carbon atoms and carbenes, e.g. the 1,4-addition to conjugated dienes is preferred). There are also contributions on
five-membered hetarynes ( M . G. Reinecke, 160 pp., intermediates with formal triple bonds in furan, pyrrole and
thiophene rings are rarer than previously assumed. Many
reactions for which such intermediates were postulated
take other pathways, which are critically reviewed here;
reactions where genuine hetarynes are formed are differentiated) and on the mechanism of the Favorskii rearrangement (A. Baretta and B. Waegell, 58 pp., where the influence of stereochemistry and of the ring strain of the ahaloketone on the course of the reaction is interpreted by
varying participation of cyclopropanone and oxyallyl intermediates).
All the contributions are by experts who have experimental experience in their fields. It is apparent to the
reader that the investigation of reactive intermediates is
progressing quickly and with high standards, even though
the spectacular achievements of the pioneer era are absent.
The broad range of topical, thorough and critical reviews
makes this work a worthwhile addition to every chemical
library. The fact that he must pay the full price, even
though only one or two articles may interest him personally, may deter the private purchaser. If he buys inspite of
this he will be rewarded by a stimulating view “over the
garden fence”.
Wotfgang Kirmse [NB 581 IE]
Angew. Chem. 1nt. Ed. Engl. 22 (1983) No. 5
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