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Book Review An Introduction to Synthesis Using Organocopper Reagents. By G. H. Posner

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BOOK R E V I E W S
An Introduction to Synthesis Using Organocopper Reagents.
By G. H . Posner. J. Wiley & Sons, Chichester 1980. xvii,
140 pp., bound, L 12.50.
The subject of the monograph and the author’s name
could give rise to misunderstanding: it is in no way a review like Posner’s two contributions that appeared in “Organic Reactions” 119, 1 (1972) and 22, 253 (1975)l. The
principal aim here is to show how an organic synthesis is
planned and on what basis a choice between several possible solutions is made. The reader takes part in a course of
instruction organized from beginning t o end on the basis
of practical examples. About 30 syntheses of aromas and
flavors, growth substances, pheromones, alkaloids, sugars,
phenols, lactones, sesquiterpenes, prostaglandins, and steroids are dealt with one by one. The copper reagents enjoy
a privileged role as a means to this end, but occasionally
another organometal compound may prove to be more
useful and often in fact a quite different approach may
well be superior.
The examples have been carefully chosen and are expertly explained. Slight uncertainties appear to exist on
stereochemical questions. Thus, in connection with a synthesis of muscalure, the sex attractant of the housefly, it is
assumed that the Wittig reaction permits its preparation
only with Z / E ratios of about 85 :15 (p. 69), while since
1966 a procedure has been known which ensures more
than 99% cis-selectivity. In discussing manicon, an ant pheromone, an important point is left unmentioned (p. 81):
the compound contains an asymmetric carbon atom. Any
synthesis will be judged beforehand on how it handles the
problem of leading to a pure enantiomer.
To stimulate the reader toward more basic reading and
independent study, about a dozen references are given at
the end of each example. No single synthesis is given in all
its details; in each case only the basic features of possible
strategies are explained. In view of this policy, it is surprising to find at the end of the monograph, as an appendix,
four small detailed experimental procedures. The historical review given in the introduction also falls somewhat
outside the framework of the book. With a length of under
ten lines, it is not exhaustive. Several studies that together
with others probably gave the impetus to the later extensive systematic investigation of copper reagents have
passed unquoted (e.g. G . Kiibrich et al., J. Organornet.
Chem. 6, 194 (1966); T. Kaufmann et al., Angew. Chem.
79, 101 (1967); Angew. Chem. Int. Ed. Engl. 6, 85 (1967);
G . Wittig et al., Justus Liebigs Ann. Chem. 704, 91
(1967)).
The monograph is short but lively, careful, and intelligent. An exhaustive subject and author index facilitates
reference to the literature. With excellent presentation and
illustrations, the publishers have done their part toward
contributing to the great pleasure with which one leafs
through the book. It will please anyone who can wax enthusiastic about synthesis, and it will probably prove particularly suitable as a basis for group seminars.
Manfred Schlosser [NB 547 IE]
Schwingungsfrequenzen I. Hauptgruppenelemente. By J.
Weidlein, U. Miiller, and K . Dehnicke. Thieme Verlag,
Stuttgart 1981. xii, 339 pp., bound, DM 88.00.-ISBN 313-567201-8
Genitourinary Reconstruction with Prostheses. By L. V.
Wagenknecht. W . L. Furlow, and J. Auvert. Thieme Verlag, Stuttgart 1981. ca. 256 pp., bound, ca. DM 80.00.ISBN 3-13-588401-5
Makromolekiile. By H.-G. Elias. Hiithig & Wepf Verlag,
Heidelberg 1981. 4th edit. xxxvii, 1097 pp., bound, D M
192.00.- ISBN 3-7785-0677-3
Fachstudium Chemie- Arbeitsbuch 6. Chemische Kinetik.
By R. Ebisch, E. Fanghanel, W.-D. Habicher, R. Hahn,
and K . Unverferth. Verlag Chemie, Weinheim 1981. 212
pp., bound, D M 36.00.--ISBN 3-527-25000-0
Elements of Quantum Chemistry. By R. Zahradnik and R.
Polak. Plenum Press, New York 1980. 462 pp., bound, $
39.50.-ISBN 0-306-3 1093-7
Insulin- Chemistry, Structure and Function of Insulin and
Related Hormones. Edited by D. Brandenburg and A .
Wollmer. d e Gruyter, Berlin 1980. xviii, 752 pp., bound,
DM 170.00.-ISBN 3-1 1-00-81-56-3
Solid State Reactions. By H . Schmalzried. Verlag Chemie,
Weinheim 1981. 2nd edit. x, 254 pp., bound, D M
98.00.-ISBN 3-527-25872-8
Aspekte von Kraftfeldrechnungen. By 0.Ermer. W. Baur
Verlag, Miinchen 1981. 619 pp., bound, D M 48.00.ISBN 3-88410-006-8
Biochemistry of Antimicrobial Action. By T. J. Franklin
and G . A . Snow. Chapman and Hall, London 1981. 3rd
edit. xi, 217 pp., bound, E 7.50.-ISBN 0-412-22450-X
Surfactant Science Series-Vol. 11. Anionic Surfactants.
Physical Chemistry of Surfactant Action. Edited by E.
H . Lucassen-Reynders. Marcel Dekker, Basel 198 1. xi,
412 pp., bound, SFr 148.00.-1SBN 0-8247-1017-7
Nutzpflanzenkunde. Nutzbare Gewachse der gemaf3igten
Breiten, Subtropen und Tropen. By W . Franke. Thieme
Verlag, Stuttgart 1981. 2nd edit. x, 470 pp., bound, ca.
DM 30.00.--ISBN 3-13-530402-7
Angew. Chem. Int.
Ed. Engl. 20 (1981) No. / I
Organic Synthesis-Today & Tomorrow. Edited by B. M.
Trost and C. R. Hutchinson. Pergamon Press, New York
1981. x, 354 pp., bound, $90.00.-ISBN 0-08-025268-0
989
Surfactant Science Series-Vol. 5. Detergency. Theory and
Test Methods. Part 111. Edited by W. G . Cutler and R. C.
Davis. Marcel Dekker, Basel 1981. x, p. 729-p. 1060,
bound, SFr. 118.00.-ISBN 0-8247-6982-1
Messen, Steuern und Regeln in der Chemischen Technik.
Edited by J . Hengstenberg, B. Sturm, and 0.Winkier.
Springer-Verlag, Berlin 1981. 3rd revised edit. xii, 500
pp., bound, DM 210.00.-ISBN 3-540-10092-X
Chemistry and Physics of Carbon. Vol. 17. Edited by P. L.
Wdker, Jr. and P. A . Thrower. Marcel Dekker, Basel
1981. xii, 304 pp., bound, SFr. 120.00.-ISBN 0-82471209-9
Methoden der Organisthen Chemie.
Band IV/ld: Reduktion, Teil 11.
Thieme Verlag, Stuttgart 1981. 4th
Ca. 1000 pages, bound, ca. DM
201 104-5
Inorganic Chemistry. By A . G. Sharpe. Longman, London
1981. xv, 682 pp., bound, E 11.95.-1SBN 0-582-450802
Organic Photochemistry. Edited by A . Padwa. Marcel
Dekker, Basel 1981. x, 502 pp., SFr. 160.00.--ISBN 08247-1345-5
Polymer Chemistry. An Introduction. By R. B. Seymour
and C . E. Carraher, Jr. Marcel Dekker, Basel 1981. xvi,
564 pp., bound, SFr. 80.00.-ISBN 0-8247-6979-1
Synthetic Reagents. Vol. 4. Mercuric Acetate, Periodic
Acid and Periodates, Sulfuryl Chloride. Edited by J. S .
Pizey. John Wiley & Sons, Chichester 1981. 426 pp.,
bound, E 32.50.--ISBN 0-470-27133-7
Progress in Pesticide Biochemistry. Vol. 1. Edited by D . H .
Hutson and T. R . Roberts. John Wiley 8~Sons, Chichester 1981. xi, 346 pp., bound, E 24.00.--ISBN 0-47127290-X
Handbuch der Praparativen Anorganischen Chemie, Vol. 3.
Edited by G. Brauer. Enke Verlag, Stuttgart 1981. 3rd
Edit. xiv, pp. 1407-2113, bound, DM 288.00 (all three
volumes must be ordered). - ISBN 3-432-87823-0
Oxygen and Life. Second B O C Priestley Conference. Issued by The Royal Society of Chemistry, London 1981.
Special Publication No. 39. xii, 224 pp., bound, E
11.00.-ISBN 0-85186-825-8
Aliphatic and Related Natural Product Chemistry. Vol. 2.
Senior Reporter: F. D. Gunstone. The Royal Society of
Chemistry, London 1981. xiii, 265 pp., bound, E 40.00.ISBN 0-85186-652-2.-A volume of the series “Specialist
Periodical Reports”
Inorganic Biochemistry. Vol. 2. Senior Reporter: H . A . 0.
Hill. The Royal Society of Chemistry, London 1981. xiv,
347 pp., bound, E 40.00.-ISBN 0-85186-555-0.-A volume of the series “Specialist Periodical Reports”
Reyrsrered names. rrademorks. erc used
0Vcrlag Chemie GrnbH,
in
In sechzehn Banden.
Edited by H . Kropf.
completely new edit.
780.00.-ISBN 3-13-
Elektrochemie 11. Elektrodenprozesse, Angewandte Elektrochemie. Taschentext 42. By C. H . Hamann and W .
Vielstich. Verlag Chemie, Weinheim 1981. xv, 428 pp.,
bound, DM 52.00.--ISBN 3-527-21081-4
Lexikon alchemistisch-pharmazeutischer Symbole. By W.
Schneider. Verlag Chemie, Weinheim 1981. 2nd edit. 140
pp., bound, DM 38.00.-ISBN 3-527-25898-1
Polarographische Analyse. By M . GeiJler. Verlag Chemie,
Weinheim 1981. 1st edit. 194 pp., bound, DM 73.00.ISBN 3-527-25887-6
Hazards in the Chemical Laboratory. Edited by L. Brefherick. The Royal Society of Chemistry, London 1981. 3rd
edit. xxi, 567 pp., bound, E 15.00.-ISBN 0-85186-4198
Reactivity of Metal-Metal Bonds. ACS Symposium Series
No. 155. Edited by M. H. Chisholm. American Chemical
Society, Washington 1981. 327 pp., bound, $ 39.00.ISBN 0-8412-0624-4
Handbook of Automated Analysis. Continuous Flow Techniques. By W. A . Coakley. Marcel Dekker, Basel 1981.
xii, 144 pp., loose-leaf SFr. 55.00.-ISBN 0-8247-1392-3
Dielectric Properties of Binary Solutions. A Data Handbook. By Y. Y. Akhadov. Pergamon Press, New York
1981. 475 pp., bound, $ 112.50.-ISBN 0-08-023600-6
Analytical chemistry of Polycyclic Aromatic Compounds.
By M . L . Lee, M . V. Novotny, and K . D . Bartle. Academic Press, New York 1981. xi, 462 pp., bound, $
60.00.- ISBN 0-12-440840-0
Tabellen zur Strukturaufkllrung organischer Verbindungen
mit spektroskopischen Methoden. Anleitungen fur die
chemische Laboratoriumspraxis, Band 15. By E. Pretsch.
T. Clerc. J. Seibl, and W. Simon.Springer-Verlag, Berlin
1981. 2nd edit. ix, 316 pp., bound, DM 39.80.-ISBN 3540-10556-5
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Angew. Chem. Int Ed Engl. 20 (1981) No. I I
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