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Book Review Chemistry of Tin. Edited by P. J. Harrison

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ods used for preparing linear oligopyrroles with two to six
units in the chain, using the “synthone approach”, and these
are illustrated by appropriate examples. Chapter 7 deals with
the physical (mainly spectroscopic) properties of oligopyrroles. Although there is some overlapping here with the
contents of Chapter 5, the reader is unlikely to consider this
as a disadvantage. Finally, in Chapter 8, the reactivity of
oligopyrroles and bile pigments is discussed under the different types of reactions (photochemical rearrangements, the
formation of metal chelates, substitution and addition reactions, etc.). The bibliography and the author and subject
indexes, which have been very carefully compiled, reinforce
the excellent impression obtained from this book. The figures, which have been prepared using an Apple-Macintosh
computer program, are excellent and essentially error-free.
In the few exceptions to this (Figs. 3.17,5.96,6.197-198) the
attentive reader should have no difficulty in correcting the
mischief of the “printer’s devil”. Altogether this is an excellent book, which will be indispensable to every chemist
working in this field, and to those wishing to become involved.
Albert Gossauer [NB 1028 IE]
Department of Organic Chemistry
University of Fribourg (Switzerland)
Carbon-13 NMR of Flavonoids. (Series: Studies in Organic
Chemistry, Vol. 39). Edited by P. K . Agrawal. Elsevier,
Amsterdam 1989. 564 pp., hardcover, DFI 350.00.-ISBN 0-444-87449-6
Flavonoids occur widely in plants as pigments and other
constituents, and are very important not only in food technology, pharmacology and chemotherapy, but also as key
substances in the chemotaxonomy of plants. Because of their
wide variety of structures their identification and structural
elucidation requires unambiguous spectroscopic methods.
To the earlier monograph and data compilation The
Flavonoids, edited by J. B. Harbone and T J Mabry and published in 1975, is now added this volume by P. K . Agrawal
and coauthors on the 13C NMR data, which supplements
and updates the earlier work.
The introduction briefly describes and compares the most
important spectroscopic methods that have been used to
determine flavonoid structures (IR, UV, MS, ‘H NMR),
then leads into the subject of the book by revising the structures of a few well-known flavonoids on the basis of their
3C NMR spectra. A useful guide is provided by tables listing typical ‘H and 13CNMR chemical shift ranges and coupling constants. Chapter 2 deals very briefly with the most
important one- and two-dimensional NMR techniques, including decoupling procedures and correlation spectroscopy
and with chemical aids for assigning 3CNMR signals (shift
reagents, labeling methods, derivatizations). Even the offresonance decoupling method, now completely superseded
by more sensitive and unambiguous methods for determining CH multiplicities (notably DEPT), is revived yet again.
Chapters 3 to 9 (altogether 414 pp.) constitute the largest
and most useful part of the book, in which over 800 literature
references are reviewed. These chapters provide a survey, in
the form of tables accompanied by a concise commentary, of
3C chemical shifts for flavonoids and anthocyanidines
(Chapter 3), isoflavonoids, coumarins, pterocarpanoids and
rotenoids (Chapter 4), neoflavonoids, auronoides and homoisoflavonoids (Chapter 5), flavonoid-glycosides (Chapter
6), chalconoides (Chapter 7), and flavanoids and flavanoid-
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glycosides (Chapter 9). The final chapter of the book gives
useful advice on using 3C chemical shift data to distinguish
between the different classes of flavonoids, and to recognize
functional groups and determine their position. Regrettably,
though, the chapter omits to explain that, by analyzing contour diagrams from two-dimensional correlation experiments such as CH-COSY and CH-COLOC, a complete and
precise structure elucidation can be obtained even with only
a small amount of substance.
The literature up to 1987 is covered. Unfortunately the
clarity of the presentation is marred by the fact that the
formulas (usually without numbering of the carbon nuclei)
are widely separated from the data tables, necessitating constant leafing back and forth. A more user-friendly arrangement would have been to give the chemical shift values directly alongside the carbon nuclei in the formulas, a form of
presentation that could have been achieved by using commercially available text-graphics software. This would also
have enabled the 6(’H) values to be clearly shown as complementary data, especially as it is nowadays possible to rapidly
determine 6(13C) and 6(’H) values in a single correlation
experiment (CH-COSY). It would also have been useful to
include details of the use of 3JcHvalues for determining substitution patterns (pp. 509f).
The subject and compound indexes have been badly printed in a 9-point matrix format. In the compound index it
would have been better to use the Chemical Abstracts method of classification (basic skeleton and substituents). Lastly,
the formulas have evidently been reproduced from the authors’ hand-drawings; the use of such technically inferior
methods is inappropriate in such a highly priced book. Nevertheless, the book is a useful work of reference for all those
concerned with identifying flavonoids and elucidating their
structures.
Eberhard Breitmaier [NB 1066 IE]
Institut fur Organische Chemie und Biochemie
der Universitat Bonn (FRG)
’
Chemistry of Tin. Edited by P. J. Harrison. BIackie, Glasgow 1989. xi, 461 pp., hardcover, s 75.0(tISBN 0-21692496-0.
Organotin Chemistry. (Series: Journal of Organometallic
Chemistry Library, Vol. 21). By I. Omae. Elsevier, Amsterdam 1989, viii, 356 pp., hardcover, DFI 270.00.ISBN 0-444-87456-9
Organotin Compounds in Organic Synthesis. Edited by Y.
Yamamoto. Tetrahedron Symposia-in-Print 36, Vol. 45,
No. 4, pp. 909-1230. Pergamon, Oxford 1989.-ISBN
0040-4020
“Tin for organic synthesis” is the best way of describing
the rapid developments that have occurred in organotin
chemistry. These developments were initiated by acknowledged masters of the art of dealing with complex organic
molecules and their subtle stereochemistry, chemists such as
E. .I
Corey, D. H . R. Barton, G. Stork and J. K . Stille. The
irony of this development is that most of the basic organotin
reactions now used had been known in the literature for
twenty years or more, though without having been exploited
to such an extent. The rift that had developed between
“pure” organic chemistry and organometallic chemistry,
and had almost become a tradition-although such a rift did
not yet exist in the days of Victor Grignard, Karl Ziegler and
Georg Wittig--was only closed again when the great “back
to synthesis” movement began.
057Q-O833]90Io9o9-lo72$3.50+ .25/0
Angen. Chem. Inr. Ed. Engl. 29 (1990) No. 9
Thus we now have four books on the subject. The first, by
Pereyre, Quintard and Rahm, which was reviewed by the
unforgettable J. K. Stille (Angew. Chem. 100 (1988) 314;
Angew. Chem. Int. Ed. Engl. 27 (1988) 445), had the misfortune to appear just at the beginning of the phase of most
rapid development (it covered literature up to early 1985).
Important advances occurred soon afterwards, and a thoroughly revised new edition would be welcome.
The book edited by Phil Harrison, covering the literature
up to 1987, has the encyclopedic layout of a classic monograph. It contains good thorough compilations of relevant
material on the spectroscopy, structure, formation and
breakdown of tin compounds, on the basic reactions involving tin, and on its biochemistry, industrial applications, etc.
A great deal of information has been carefully compiled and
critically evaluated with clear figures and tables. Printing
errors are rare, except possibly in the names of authors, e.g.
in the preface (Poller), while on page 17 two references have
become jumbled together under (i), and the name of this
reviewer got lost. The formulas are easily legible, and the
presentation is attractive. The main emphasis is on structural
chemical aspects, in accordance with the interests of the editor. Preparative applications, on the other hand, are relegated to the background. In some places the editor has not
succeeded in fully coordinating the contributions of the
different authors, as often happens in works of this kind,
despite the fact that all are British. For example, overlapping
occurs between Chapter 9 (Radical Chemistry of Tin, A . G.
Davzes)and Chapter 20 (The Uses of Organotin Compounds
L. Wardell), despite the fact that
in Organic Synthesis, .I
these contain only 20 and 43 pages respectively. One could
have wished for both these authors to be given more space,
but it is not obvious to the reviewer where economies
of space could be made elsewhere in the book without a
sacrifice of information that would detract from the encyclopedic value of the book. Thus it is fortunate for readers
interested in preparative aspects (and the number of these
has increased in the last few years) that there also exist the
two other books discussed below.
The book by I. Omae covers the literature up to 1987, and
partly that of 1988. Although it deals with the classical principles of syntheses and reactions involving the tin atom (including, for example, a good treatment of the direct synthesis
of organotin compounds from elemental tin), greater emphasis is put on the important developments of the last few
years, e.g. palladium catalyzed reactions using organotin
reagents are covered in detail. However, aspects that can be
criticized are a degree of unevenness in the treatment, and
some arbitrariness in the choice of topics emphasized. For
example, whereas free radical reactions using R,SnH are
adequately covered in total in Sections 5.3 and 5.4 of Chapter 5 (“Reactions of Organotin Compounds”) and 6.9 of
Chapter 6 (“Organic Synthesis with Organotin Compounds”, meriting a full chapter of 47 pages), intramolecular
coordination in P-carbonylstannanes is given a disproportionately large amount of space in Chapters 3, 6 and 7, despite the fact that a book on this topic by the same author
appeared in the same series of monographs in 1986. This
leads to quite a lot of repetition. In Chapter 6 under aryl
stannanes one fails to find the early electrophilic scission
reactions (studied by C. Eaborn and others) which are the
foundation of modern syntheses. In view of current public
concerns it is surprising not to find the keyword “toxicity”,
even though there are individual mentions of this scattered
through the book, e.g. under “Biological Activities”. Under
environmental aspects the outstanding analytical studies by
F Brinckman deserved to be mentioned. However, these
Angew. Chum. hi.Ed. Engl. 29 (1990)No.9
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comments should not be allowed to detract from the author’s achievement in having provided a lucid survey of the
rapidly growing knowledge in this field. The book is mainly
intended for organic, organometallic, pharmaceutical and
industrial chemists involved in research, and is also suitable
for advanced students.
However, the publishers must be reproached for the poor
standard of production at such an inflated price. The presentation of the text in typescript form, unedited and without
any emphases, variations of typography, or bold or italic
type, and the clumsy formulas etc., are not reader-friendly.
The user will find the book reminiscent of a hand-produced
doctoral thesis of 30 years ago. And this in a book which is
also recommended for use by students! Any modern program for printing text and formulas on a standard desk
computer offers better readability than this.
The Tetrahedron Symposium-in-Print edited by Yoshinori
Yamamoto is devoted entirely to the use of organotin compounds in organic synthesis, and covers the literature up to
1988. An excellent treatment of the subject is given, with
original laboratory recipes, under a number of very well
chosen sub-areas. There are 28 articles by expert authors,
most of whom are leading participants in the current rapid
developments in the field. To meet ideal criteria the book
should perhaps also have included contributions by M .
Reetz and G. E. Keck-and from the editor himself! However, this is a very good, timely and relevant report on a
rapidly expanding field.
Which of these books ought one to buy? In most cases two
are needed. No true student textbook is available. Harrison’s
book is the encyclopedia of the subject, but is too short on
detail for organic synthetic purposes. The book by Omae is
better in this respect, but contains less information of a general nature. Yamamoto’s book is aimed especially at synthetic chemists. One must choose according to one’s point of
view and objectives.
Wilhelm Paul Neumann [NB 1064 IE]
Institut fur Organische Chemie
der Universitat Dortmund (FRG)
Leukotrienes and Lipoxygenases. Chemical, Biological and
Clinical Aspects. (Series: Bioactive Molecules, VoI. 11).
Edited by J. Rokach. Elsevier, Amsterdam 1989. xxxii,
518 pp., hardcover, DFl360.00.-ISBN 0-444-87464-X
The importance that the arachidonic acid derivatives have
earned as highly effective, physiologically and pharmacologically active mediators of intercellular communication has
led to the coining of the collective term “eicosanoids”.
Whilst the initial main interest was in the prostaglandins, the
new eicosanoid research has shifted to the area of lipoxygenases and leukotrienes. The elucidation of their chemical
structures and the biochemical characterization of their
biosynthesis and mode of action provided the key for the
development of inhibitors for which high hopes are held out,
since the lipoxygenase products are involved in the activation of the immune system. Pioneering studies have mainly
been carried out by three groups (Harvard, Quebec and
Stockholm). Of their publications, this one by J. Rokach
(Merck Frosst, Canada), in Volume 11 of the “Bioactive
Molecules” series, has attempted to collect and critically review all the information obtained to date.
This first attempt at the task has been an outstanding
success. Together with 15 coauthors, Rokach has systematically brought together all aspects of this material, from
Vurlagsgesellscha~mbH, D-6940 Weinheim. 1990
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