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Book Review Dienes in the Diels-Alder Reaction. By F. Fringuelli and A. Taticchi

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Dienes in the Diels-Alder Reaction. By E: Fringuelli and A .
Taticchi. Wiley, Chichester, 1990. xx, 348 pp., hardcover
E 55.15.-1SBN 0-471-85549-9
Within its 348 pages this book offers no fewer than
165 pages of tables and 63 pages of references. While this
may be taken as evidence of the authors’ great diligence, it
does not make up for the fact that the presentation of the
data leaves much to be desired. In their preface the authors
indicate that the audience they have in mind includes undergraduate students. Such students should be warned, however, that this book, at the steep price o f f 55, is not a good
investment, since only the first of its six chapters can be
considered didactic. The first chapter does indeed contain a
discussion of the fundamental principles of the Diels-Alder
reaction, but since the treatment is somewhat superficial and
is compressed into 40 pages, it would have been preferable to
omit this chapter altogether and, by way of introducing the
subject, to refer the reader to an appropriate and well-received textbook, such as that by W Carruthers,[*] a recent
text that also happens to be less expensive since it is available
as a paperback (US $36.01 paperback, US $73.01 hardcover).
Probably most readers will lose interest in the book after
the first chapter. That is where the enumeration begins of
1,3-dienes and their reactions with various dienophiles. The
organization is conventional: open chain dienes (Chapter 2),
exocyclic dienes (Chapter 3), compounds with one exocyclic
and one endocyclic double bond (Chapter 4) and with two
endocyclic double bonds, each in a different ring (Chapter 5),
and finally, cyclic dienes (Chapter 6). Each of these classes of
dienes is introduced by means of representative reactions
and individual reactions are then described in extensive tables. In the tables the diem component is listed by structure,
whereas each dienophile is described in two ways: firstly,
either by full name or by an abbreviation, and secondly by a
code classifying reactive centers and substituents. The purpose of this latter listing escapes me.
It is difficult for a reviewer to assess whether the collection
of data presented in this volume is really comprehensive. In
trying to do so I chose 20 relevant references between 1980
and 1986, which are known to me, but found only 12 of them
referred to in the book. Older references cannot be traced
here; it was made quite clear in the preface that the literature
is covered only between 1978 and 1987. Nevertheless, the
extensive tables which list reactants and yields may be useful
to academic or industrial research chemists who wish to
check their own literature surveys.
This volume is presumably based on an extensive search of
Chemical Abstracts. Unfortunately, the references so collected were not placed in any systematic order whatever,
alphabetic, numerical or chronological. Thus, Chapter 2 lists
500 references but its first section, 2.1 (1,3-butadienes), starts
with reference 456. In Chapter 6 each of the three sections is
referenced independently. The first section of this chapter,
6.1 (cdrbocyclic dienes) (453 references), starts with reference 413. All this is annoying, particularly since many cheap
computer programs are available that can execute alphabetical or numerical sorting with ease. With reference to computer software, apparently several different programs of
varying quality were employed to draw the formulas in this
book: in some cases double bonds are not clearly drawn
(e.g., pp. 152, 233, 237), and several drawings are smudged
[*] W. Carruthers, Cycloaddirion Reucfrons in Organic Synlhesis, Pergamon,
Oxford, 1990. 300 pp.. hardcover ISBN 0-08-034713-4, paperback.
364
8
VCH Verlugsge.~ells~hu~
mbH, W-6940 Wernheim,1992
(e.g., the representations of face-selective Diels-Alder reactions, pp. 38 and 63).
What a pity: a great deal of work has gone into this volume, but not enough thought was given to its design and
execution.
Axel G. Griesbeck
Institut fur Organische Chemie
der Universitat Wiirzburg (FRG)
Sulfur Analogues of Polycyclic Aromatic Hydrocarbons
(Thiaarenes). Environmental Occurrence, Chemical and
Biological Properties. (Series: Cambridge Monographs on
Cancer Research.) By J Jacob. Cambridge University Press,
Cambridge, 1990. XIV, 281 pp., hardcover E 55.0. - ISBN
O-j21-30120-3
This monograph provides chemists, biologists, and medical scientists with information on the sulfur analogues of
polycyclic aromatic hydrocarbons, with special regard to
their possible environmental effects, in particular their mutagenic and carcinogenic properties. It includes analytical and
synthetic aspects, as well as the physical and biological data
that are available up to now. As the information on these
topics is widely scattered throughout the literature, the authors have performed a valuable service in bringing it together in an encyclopedic compilation, and in presenting. for the
first time, comparisons with the corresponding non-sulfur
polycyclic arenes that have been studied more thoroughly.
Nevertheless, because there are still many gaps in our knowledge of these sulfur compounds, this cannot be more than a
first crude attempt. Since many new sulfur-containing polycyclic arenes have recently been synthesized, one must hope
that it will soon be possible to fill in the picture in more
detail, and to find out whether the sulfur analogues are in
fact less carcinogenic than the corresponding arenes.
The monograph is written in a concise and clearly understandable style. It begins with a general part (94 pp.) which
gives information on the biological activities of this hitherto
relatively little studied class of compounds, deals with questions of nomenclature, and discusses spectroscopic data
(UVjVIS, fluorescence, phosphorescence, IR, NMR, mass
spectrometry); in some cases these data are presented in the
form of tables together with those for the corresponding
non-sulfur arenes. This first part also includes general information on the synthesis of the compounds and their isolation, separation and identification, based on oxidations or
reductions in combination with a wide variety of chromatographic methods. The picture is completed with information
on natural occurrence and on mutagenic formation from the
biomass. The biosynthetic building blocks are believed to be
hydrogen sulfide from microbial processes, elemental sulfur,
and sulfur-containing amino-acids. This explains the instances of occurrence in mineral oil and coal. A carefully
compiled bibliography, including also metabolic aspects, is
provided.
The second part (132 pp.) gives information on individual
thiaarenes. The choice seems rather subjective, but has been
determined by the relevance to biological activity. Unfortunately the monocyclic compound thiophene is not included.
The compound-specific part begins with bicyclic and ends
with nonacyclic compounds. There is a general preponderance of thiaarenes with the sulfur atom in the five-membered
ring, i.e. thiophene derivatives. Only a few isolated examples
of thiapyrans are included. One quickly gets used to the
peculiar notation used for the partial structural formulas.
0570-0833/92/0303-0364$3.50+.25/0
Angew. Chem. I n f . Ed. Engl. 31 (1992) No. 3
*
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