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Book Review Comprehensive Heterocyclic Chemistry. The Structure Reactions Synthesis and Uses of Heterocyclic Compounds. Cochairmen of the editorial board A. R. Katritzky and C. W

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BOOK R E V I E W S
Comprehensive Heterocyclic Chemistry. The Structure,
Reactions, Synthesis and Uses of Heterocyclic Compounds. Cochairmen of the editorial board: A . R. Katritzky and C. W . Rees. Pergamon Press, Oxford 1984,
bound. $ 2200.00.-ISBN (complete work) 0-08-026200-7
Vol. I : Part 1 : Introduction, Nomenclature, Review Literature, Biological Aspects, Industrial Uses, Less-common
Heteroatoms. Editor: G. Meth-Cohn. xvi, 731 pp.-Vol. 2:
Part 2a: Six-membered Rings with One Nitrogen Atom.
Editors: A . J . Boulton, A . McKillop. xiv, 689 pp.-Vol. 3:
Part 2b: Six-membered Rings with Oxygen, Sulfur or Two
or More Nitrogen Atoms. Editors: A . J . Boulton, A . McKillop. xiv, 1210 pp.-Vol. 4: Part 3: Five-Membered Rings
with One Oxygen, Sulfur or Nitrogen Atom. Editors: C. W .
Bird, G. W. H . Cheeseman. xiv, 1195 pp.-Vol. 5 : Part 4a:
Five-Membered Rings with Two or More Nitrogen Atoms.
Editor: K . T. Ports. xiv, 994 pp.-Vol. 6: Part 4b: FiveMembered Rings with Two or More Oxygen, Sulfur or Nitrogen Atoms. Editor: K . T. Potts. xiv, 1171 p~.-Vol. 7:
Part 5 : Small and Large Rings. Editor: W . Lwowski. xiv,
867 pp.-Vol. 8: Part 6: Indexes. Editor: C. J. Druyton.
xiv, 1111 pp.
A great, and still rapidly increasing, number of heterocyclic compounds is known; this makes it progressively
more difficult to obtain a survey of particular aspects of
this field, which is so important in synthesis, in biochemistry and in its many practical applications. Attempts at
orientation in this mass of material by means of textbooks
often founder on account of the selective or even uninterested coverage given to heterocycles. As far as specialized
literature goes, “Elderfield”, which largely stems from the
1950’s, can only be conditionally considered and even the
60+ volumes of “Weissberger-Taylor” are not all u p to
date. The present monumental work sets out to fill an obvious gap in the market. Formally, it complements the series “Comprehensive Organic Chemistry” and “Comprehensive Organometallic Chemistry” (cf. Angew. Chem. In/.
Ed. Engl. 22 (1983) 797). Heterocyclic chemistry is dealt
with here in more than 6000 pages by over 120 authors,
predominantly from English speaking countries. From the
FRG K . Dimroth. W . Flitsch, W. Friedrichsen, H . Gotthardt,
H . Neunhoeffer. W. PJleiderer, I . Ugi. and H . Wumhoff
have contributed and from the G D R G. W. Fischer, E.
Schmitz, and T. Zimmermann.
The numerous applications and biological aspects of
heterocycles are prominent in the first volume. Observations on the toxicity of chlorinated dibenzodioxins (p. 118)
provide an indication of how up to date the work is. Beside
this there is a section on nomenclature (36 pages), a literature survey of heterocyclic chemistry (34 pages) and a very
informative chapter on the synthesis of non-heterocycles
from heterocycles (79 pages). The volume concludes by
treating boron containing rings (35 pages), rings containing
higher elements of groups 4 or 5 (phosphorus: 45 pages,
arsenic, antimony, bismuth: 23 pages), rings containing halogens (10 pages) and rings containing a transition metal (8
pages).
The mass of material on heterocycles containing nitrogen or a group 6 element requires clear arrangement of
the content. As is usual, ring size, together with the number
and type of heteroatoms, serves as the general criterion of
organization. To emphasise common properties, however,
annelated systems are discussed with the corresponding
monocycle. Parts 2 to 5 (Vols. 2 to 7) are each introduced
A r i q w . Cheni.
1111.
Ed h y l . 24 (1985) No. I 1
by a general chapter which gives a condensed survey and,
above all, draws out relationships between the ring systems
to be dealt with. Then follow extensive sections on the individual ring systems. Whenever possible, general and specialized chapters are subdivided as follows :
structure, especially molecular structure, as well as spectroscopic data and problems of tautomerism
reactivity of ring positions and substituents of aromatic
compounds as well as non-aromatic derivatives
synthesis from non-heterocycles, arranged according to
the number of newly formed bonds, or from heterocyclic
precursors
applications.
In the second volume pyridine and benzo-annelated pyridines are dealt with according to this general plan (95
pages survey and 422 pages specialized material). The volume is completed by short sections on quinolizinium ions
(55 pages) and pyrido-pyridines (46 pages).
The third volume is a compilation, in 17 chapters, of the
chemistry of 6-rings with at least two nitrogen atoms or
with oxygen or sulphur. Apart from (benz0)pyridazines (57
pages), -pyrimidines (98 pages), and -pyrazines (41 pages),
amongst others pteridines (64 pages), (benz0)triazines (altogether 160 pages), pyranes (306 pages) and thiopyranes
(58 pages) are dealt with in depth.
The fourth volume begins with a general introduction to
5-rings with one heteroatom (153 pages). Amongst others
(benzo)pyrroles (221 pages), -furans (18 1 pages), -thiophenes (219 pages) and -selenophenes (36 pages) are handled in individual chapters. Porphyrins, corrins and phthalocyanins (66 pages) belong in this volume too.
In volumes 5 and 6 the treatment of 5-rings is extended
to those with at least two heteroatoms. After the introduction (162 pages), the following receive substantial sections
of their own: (benzo)pyrazoles (135 pages), -imidazoles
(1 53 pages), purines (105 pages), (benz)isoxazoles ( I 30
pages) and (benz0)thiazoles (95 pages).
The seventh volume contains 15 contributions on heterocyclic 3- and 4-rings and 7 sections on rings with at least
seven members. Individual chapters are devoted to penicillins (41 pages), cephalosporins (14 pages), crown ethers
and cryptands (32 pages) and heterophanes (18 pages).
Without reference to the organizational structure, the
entire work is accessible via the four indexes of volume 8.
A “physical data index” contains sources of quantitative
information on more than 4000 heterocycles, e.g. for “furan, tetrahydro” information is supplied on the dipole moment, ‘H-,
I3C-, ” 0 - N M R spectra, microwave spectrum,
pK, value and the photoelectron spectrum. The subject index contains 40,000 entries; the author index lists 30,000
names in 35,000 references. A ring index, analogous to the
“Chemical Abstracts” register, names 4000 ring systems.
A striking characteristic of the work is that literature references are given as an alphanumeric code derived from
the year of publication, an abbreviated designation of the
journal and the page number. Thus the reference [Angew.
Chem. 95 (1983) 8191 would appear as (83AG819). This
method enables the reader to identify the most recent reference directly in the text and, after a little practice, to find
the original straightaway. The complete references are
given at the end of each volume, arranged by year of publication. The literature references reach u p to 1982; in
places publications from 1983 are also included.
1005
All in all this is a successful work; the external appearance is pleasing and every page is strewn with useful information. The rigorous arrangement of the individual volumes enables quick orientation, even without recourse to
the index, and means that cross references can largely be
dispensed with. The numerous clear formula diagrams and
informative tables are very helpful. Preparative chemists
will particularly welcome the tabular grouping of the “best
methods of synthesis”.
The production of this work must have been a Herculean task for authors and editors alike. This deserves recognition and makes detailed criticism mere niggling. Spot
tests indicate that printing errors have been carefully expunged and that transcription errors do not exceed the
sadly inevitable limits. One striking example of this is the
citation of two different (by 1.98 eV) ionization potentials
for oxetane on the same page (Vol. 7, p. 368). It is unfortunate that “oxete”, the correct name for the unsaturated 4ring ether, is replaced even in a chapter heading by “oxetene” (Vol. 7, p. 363). In a few cases the chapters have
turned out to be pretty eclectic, as, for example, when 1,2and 1,3-dioxolanes as well as 1,2- and 1,3-oxathiolanes are
discussed in tandem, although they are cyclic derivatives
of quite different classes of compounds (Vol. 6, p. 749ff).
The selection of material by authors and editors is naturally subjective and some readers will find particular aspects missing or inadequately dealt with. Obviously, however, exhaustive treatment cannot be expected even in
42 cm of shelf space. Even so a survey of the subject and
an entry into further literature are provided. The general
chapters enable interested students to find their bearings
and could also serve as the basis for a lecture; for this reason this work should enable heterocyclic chemistry to find
a place in the curriculum that corresponds to its importance. The specialized chapters are available to meet the
demand for more detailed information. Even expert-in
universities or industry-will find useful references here.
Interested parties from neighboring disciplines will appreciate the extensive sections on applications and biochemical aspects. Quite apart from searching for particular information, the book is interesting territory for the browser;
even in the age of machine readable data this “semi-systematic” access to information is indispensable and will ensure a large readership for “Comprehensive Heterocyclic
Chemistry”.
Ernst Schazrrnann [NB 709 IE]
Institut fur Organische Chemie
der Universitat Hamburg (FRG)
Gene und Klone. Eine Einfuhrung in die Gentechnologie. By
E.-L. Wznnacker. Verlag Chemie, Weinheim 1984. xii,
454 pp., bound, DM 70.00.--ISBN 3-527-26061-7
Textbooks dealing with topics in molecular biology have
a very short half-life and become rapidly outdated. Courage and the ability to foresee future developments are
therefore required when one sets out to write a detailed
introduction into the concepts and techniques of gene
technology. Ernst-Ludwig Winnacker, with his book “Gene
und Klone”, has succeeded in making a contribution that
will not only be of value to novices in the field of molecular biology. In didactically exemplary fashion, the fundamental principles of molecular biology are combined with
the concepts and techniques of gene technology. The sequence of chapters reflects the experimental procedures
routinely followed in cloning experiments. Research in
molecular biology always involves genuine craftsmanship
that has to be mastered and modified daily on the basis of
1006
the most recent developments. This practical aspect has
also been adequately dealt with by Ernst-Ludwig Winnacker’s presentation. The combination of theoretical considerations and practical instructions renders the book readable
for newcomers; accuracy in detail and the author’s efforts
to cover current findings make the book useful and worthwhile reading for advanced students as well. Essentials for
daily work are readily available by the inclusion of numerous, clearly drawn illustrations presenting genetic and
structural maps. In the appendix, the guidelines of the
“Zentrale Kommission fur die Biologische Sicherheit” are
also included. The reader should, however, be aware of the
fact that these guidelines are currently being revised.
Shortly before writing this book review, I wanted to leaf
through “Gene und Klone” again. 1 had to search for my
two copies in the laboratory. Only after days of questioning, however, was I able to find them. One copy had been
extensively used and showed it. Apparently, the book has
been consulted frequently by my younger colleagues. This
observation is perhaps the best recommendation for the
book.
In Munich, it must be difficult to compete with the
“Schonheitengalerie” of the first Ludwig.“] Although the
gallery of molecular biologists presented by the Ludwig
who writes about genes and clones may render the cold
scientific facts more likeable, its attraction is in general far
inferior to the collection of the first Ludwig.
This book is highly recommended above all to students
in the field. I hope that the book goes through many, carefully rewritten editions and will be translated into English
after having been brought up-to-date.
Walter DoerJler [NB 724 IE]
Institut fur Genetik der Universitat Koln (FRG)
Hydrazine and its Derivatives. Preparation, Properties, Applications. By E . W . Schmidt. Wiley, Chichester 1984.
xxv, 1059 pp., bound, f 87.00.--ISBN 0-471-89170-3
The major sections of this book are: the production of
hydrazine (including the anhydrous compound), together
with details of the capacities of and processes employed by
western manufactures ; physical properties ; chemical properties of hydrazine and its salts with a detailed section on
hydrazine analysis; the handling of hydrazine with a very
important subsection on its toxicology; the decomposition
of hydrazine; utilization of hydrazine, especially its use as
a rocket propellant whose description occupies more than
100 pages.
Organic derivatives are described only very briefly and,
essentially, only insofar as they are of importance to the
field of rocket propellants.
As the author, who is a senior staff scientist of the
Rocket Research Corporation and obtained his doctorate
in Tubingen, correctly states, this is the first comprehensive survey of hydrazine in an occidental language for the
last 30 years. For all who are doing work in the field of
hydrazine the absence of such a book has been a significant handicap.
Here too, as in many other fields, the literature has exploded. The reference list contains more than 4400 citations on 194 pages. The references are listed “lexically”,
that is alphabetically according to the name of the first author, so that the list fulfills some of the functions of a n
author index.
[*I
Ludwig I., King of Bavaria (1825-1848), had portraits of the most beautiful Munich women painted for his “Schonheitengalerie”, which is now
exhibited in Schloss Nymphenburg. Go and see it.
Anyew Cliem. Inr. Ed. Enyl. 24 (1985) No. I 1
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