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Book Review Beilstein Handbook of Organic Chemistry. 4th Edition. 5th Supplementary Series. Volumes 17 18 and 19. Edited by R

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BOOK REVIEWS
Beilstein Handbook of Organic Chemistry. 4th Edition. 5th
Supplementary Series. Volumes 17, 18, and 19. Edited by
R . Luckenbnch. Springer, Berlin 1984- 1988. 30 572 pp.,
hardcover. DM 90440.00
With the appearance of sub-volume 17/1, the first in the
5th Supplementary Series of the 4th Edition, in 1984 and
sub-volume 19/I 2 in 1988 all the chalcogen-containing heterocycles reported in the period 1960-1979 have now been
fully described in “Beilstein”.
This is an overwhelming work considering that in 35 subvolumes and more than 30 000 pages 200 307 individual compounds have been described. In the accompanying Subject
Index to the sub-volumes some 219296 names are listed;
however, several compounds are cited more than once under
different names. Cumulative Subject Indexes covering the
contents of Volumes 17- 19 will soon appear and should be
completed by 1990.
The contents of Volumes 17-19 cover the oxygen heterocycles. Volumes 17 (11 sub-volumes) and 19 (12 sub-volumes) deal with oxygen heterocycles with one oxygen atom
in the ring while Volume 19 (12 sub-volumes) is devoted to
the oxygen heterocycles with two or more ring oxygens. Following the traditional Beilstein system, the heterocycles containing higher chalcogens in the ring are dealt with as derivatives of the corresponding oxygen compounds and follow
them accordingly. A very useful feature is the inclusion, in
each sub-volume, of a short introduction to the Beilstein
system. With this even the unpractised user can soon locate
the compound sought for. Additional help is available in the
form of the booklet “How To Use Beilstein“ published by
the Beilstein Institute in German, English, and Japanese, and
a “German-English Dictionary” containing the most important formulations used in Beilstein. These are both available
free of charge. For those who wish to have electronic access
to Beilstein the search program “SANDRA” is available. In
this respect Beilstein has also managed a smooth transition
into modern developments and so fulfilled the needs of all
those users to whom date processing is a daily routine.
Use of the sub-volume Subject Index is facilitated by the
inclusion of a short introduction to the nomenclature used
by Beilstein. In addition, in sub-volumes 17/1, I8/l and 19/1,
a comprehensive list of the prefixes used and a dual language
explanation of the stereochemical descriptors has also been
included. These are all valuable aids, enabling one, on the
one hand, to find compounds easily in Beilstein and, on the
other, to name new compounds correctly. It would be a great
advantage if the names thus generated were accepted by the
primary publications.
An,@+!.. Chmi. lnr. Ed. Engl. 29 (1990) No. 1
C
On taking a closer look at Volumes 17-19 one finds that
industrially important compounds, e.g. ethylene oxide (subvolume 17/1), ecologically relevant substances, e.g. chlorinated dibenzodioxins (sub-volume 19/2), and natural products, e.g. steroids (sub-volume 19/3) are all represented. The
foregoing is only an indication of the wide selection of compounds which are dealt with. Precisely in the case of the
dibenzodioxins one becomes aware of the advantages of the
Beilstein system. One finds chlorinated compounds containing the dibenzodioxin skeleton, with the chlorine atoms in all
possible positions, are dealt with one after the other following the parent compound. This gives the user an overview of
related compounds which in practice allows him or her to
make a substructure search in aprinted medium. In addition,
Beilstein enables the user to see the relationships between
stereoisomers as they so often occur in natural products. In
sub-volume 19/3, for example, there are entries for seven
stereoisomeric spirostan-2,3-diols which have been described
and assigned their correct stereodescriptors.
The layout of the individual entries follows a well established pattern. Details about the constitution and configuration of a compound, which have often been clarified and
corrected by the Beilstein team after taking into consideration the latest available literature, are followed by an
account of the natural occurrence, extraction from natural
products, preparation, synthesis, and purification. It is
worth mentioning that biochemical methods are also dealt
with here if they have been used on a preparative scale.
There then comes the factual part, which is the largest and,
certainly for the user looking for data, the most important
part of the entry. Here the structure and energy parameters
as well as the physical properties, including spectroscopic
data, are presented. Special mention should be made of the
plethora of numerical data in Bedstein, which makes it one
of the largest factual databases in the world. It still has not
dawned on many chemists that a wealth of information is
tucked away in Beilstein. This should be emphasized more
strongly in future. As a result of this data collection, Beilstein
has become a link between the spectroscopic databases dealing with relatively few compounds and the bibliographic
databases of Chemical Abstracts Services (CAS). Due to the
method of indexing it is difficult to make a directed search
for data in Chemical Abstracts.
The entry continues with a description of the chemical
behavior and addition compounds and concludes with an
account of the derivatives.
Changing the language in which Beilstein is published
from German to English has made further compression in
the text of the entries possible. This is particularly noticeable
in the descriptions of preparative methods and chemical
behavior, which are presented in telegraphic style. For the
chemist who is exclusively interested in preparative work this
compression - relative to that in the earlier Supplementary
Series - may be painful. In exchange, however, he gets an
enormous increase in the amount of physico-chemical data:
this is to be welcomed. In this area especially, functions have
been assumed from which the “classic” Beilstein user can
only profit.
The “Beilstein Online Database” must also be viewed in
this light. The first part of this database (at the time of
writing) contains the heterocycles reported in the period
1830-1959 which were described in Volumes 17-27 of the
Main Series and Supplementary Series I-IV. The volumes
reviewed here form an extension to the database. Together
VCH VerIu~qesellschu/lfrmhH, 0-6940 Weinheim.1990
0570-0833i9Oji~l(~f-0109
S 02.SOjO
109
the two constitute a valuable supplement to the CAS databases.
In this connection it would be useful if the CAS Registry
Numbers were available in the text as well as in the indexes
so that one could move more easily from one reference work
to the other.
The overall impression of the volumes reviewed is excellent, and how could it be otherwise for this standard work on
organic chemistry with its new, up-to-date format? Both the
publisher and the Institute have done everything possible to
make “Beilstein” attractive to the synthetic chemist. He
should make the most of what is offered.
Heinrich Heydt, Manfred Regitz [NB 1033 IE]
Fachbereich Chemie
der Universitat Kaiserslautern (FRG)
Non-Metal Rings, Cages and Clusters. By J. D. Woollins, Wiley, Chichester 1988. ix, 124 pp., hardcover, E 25.95. ISBN 0-471 -91 592-0
The rapid progress made during the last 25 years in the
chemistry of cyclic nonmetal compounds is still not reflected
in the contents of most textbooks. This very area, however,
is particularly well suited to making students clearly aware,
at an early stage, that the chemistry of all nonmetal elements
(including carbon) forms a unified whole. Therefore, this
introductory book, which originated as the text of a lecture,
unquestionably fulfills a real need by serving as an appetizer
to this area of chemistry.
After a short presentation of the most important fundamental concepts and synthetic strategies, the following three
chapters discuss a series of exemplary nonmetal ring systems,
from electron-deficient compounds and classical (“electronprecise”) compounds to electron-rich compounds. Understandably, the limited coverage of the book necessitates a
somewhat arbitrary selection ofcompounds or, as the author
puts it, the selection “should be regarded as my choice from
a very large box of chocolates”. However, the limited number of compounds makes it possible to indicate numerous
relationships and structural similarities between different
classes of compounds. This feature is especially valuable for
students, who, all too often, organize their chemical knowledge in separate boxes according to element symbols. In this
respect, however, it would have been useful to have included
at least some examples of cyclic hydrocarbons.
The chapter on electron-deficient compounds contains a
good overview on structures, bonding, syntheses, and properties of boron-hydrogen compounds and metallaboranes.
The importance of ‘H and “ B NMR spectroscopy for structural elucidation is made clear through several representative
spectra. However, the section on polyhedral boron subchlorides is much too short, while the fragmentary treatment of
transition-metal clusters could have been omitted in view of
the book’s title.
The chapter on normal (“electron-precise”) compounds
covers the most important homo- and heterocyclic ring systems of sulfur, phosphorus, and silicon. The cyclic silicates
and metaphosphates are not mentioned, since this would
have exceeded the intended coverage of the book. Lacking in
the discussion of homocyclic silicon compounds is mention
of the three-membered ring as well as of the existence of
fused ring systems; this also holds true for the large number
of corresponding silazanes. Similarly, the discussion of phosphorus omits mention of the interesting cyclic acid anions
with P-P bonds.
The last chapter on electron-rich compounds presents a
concise discussion, illustrated by numerous formula
schemes, of what is currently known about borazenes, phosphazanes, phosphazenes, sulfur-nitrogen rings and cages,
and polychalcogen cations.
The book is directed at undergraduates with the goal of
awakening their interest in this area of molecular chemistry.
Helpful in this respect is the list of references, in particular
key review articles, at the end of each chapter. Furthermore,
the two-volume work of Haiduc-Sowerby is recommended as
a source of additional information.
Not surprisingly, the treatment of such a huge amount of
information and the attempt to systematize it leads to some
errors. Apart from obvious typographical errors (like the
name Gillespie on page 5), these can sometimes lead to confusion, especially for students. For example, on page 7, the
formation of P,H, from P,H, is not a polymerization. On
page 15 (sixth line from the bottom), electron pairs would be
correct; on page 49, dichlorodisulphane; on page 54, P,H,
and P,H,; on page 55 in Fig. 3.1 1, Li,P,,; and on page 67 in
Fig. 3.18, P,0,30. The “equation” for the synthesis of P,H,
(page 54) is incomprehensible and the formation of P,Me,
(page 55) is not a redox reaction with evolution of elemental
chlorine. In addition, several references to the literature contain errors.
Despite these privisos, this highly readable book offers an
initial, informative overview of the heterogeneous area of
cyclic nonmetal compounds and is also suitable as an introduction to those wanting to study nonmetal rings and cages.
Moreover, chemists interested in preparative and structural
chemistry will find the book highly interesting. The book is
excellent in appearance, although somewhat overpriced.
Marianne Baudler [NB 1039 IE]
Institut fur Anorganische Chemie
der Universitat Koln (FRG)
Industrial Inorganic Chemistry. By W Biichner, R. Schliebs,
C . Winter and K. H . Biichel. Translated by D. R. Terrell.
VCH Verlagsgesellschaft, Weinheim/VCH Publishers,
New York 1989. 614pp., hardcover, DM 145.00. ISBN 3-527-26629-1 10-89573-610-1
This English translation of a 1984 German edition has
been updated and supplemented with data from the US.
industrial inorganic chemicals market. The original authors
were all with Bayer AG in 1984, and have produced a book
which includes a broad range of “technical chemistry”. It is
organized into “primary inorganic materials” (H,, H,O,
peroxides, N-compounds, P-compounds, S-compounds,
halogen compounds, metals and their compounds), then into
product classes (mineral fertilizers, silicones, zeolites, inorganic fibers, construction materials, ceramics, wear-resistant
materials, pigments) as well as nuclear fuel principles and
production. The organization by element makes it ideal for
lecturers wishing to illustrate an inorganic chemistry course
with applications (e.g., video cassettes, optical fibers, microelectronic devices).
The advertising claims that economic aspects, process energy balance and ecological consequences are treated, and
that the intended use is not only the classroom (abundant
marginal notes repeat central points of the text), but also in
business and law. Indeed, there is an abundance of tables of
workable terrestrial reserves, of production, and of consumption (e.g., annual asbestos production, by country, to
six significant digits!). Ecological matters are treated only
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