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Book Review Carbon-13 NMR of Flavonoids. (Series Studies in Organic Chemistry Vol. 39). Edited by P. K

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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-
’
1072
8 VCH
Verlugsgesellschufi mhH, 0-6940 Weinhein?, 1990
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
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