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Book Review Nitration. Methods and Mechanisms (Organic Nitro Chemistry Series). By G. A. Olah R. Malhotra and S. C

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plexes with C , symmetry, offers an interesting detailed insight into the development work needed to achieve spectacular successes of this kind.
The last contribution in the book describes the structures
of zeolites and ways of modifying them for specific purposes,
then indicates how they can be used for organic syntheses; up
to now these have been used mainly on an industrial scale for
producing basic chemicals.
Altogether the book is a very useful guide to the subject of
catalysts in organic synthesis, which has a promising future;
in particular it offers beginners a straightforward introduction to this field. All the articles are competently written and
thorough, and are therefore likely to be frequently cited. It
would be difficult at present to find other reviews presenting
the current state of knowledge in such a concentrated form.
One can only hope that the price, which has increased further
to DM 78.00-too much for a paperback in my view-will
not prevent this interesting book from reaching a wide readership that will include students.
Hans4 Altenbach [NB 1051 IE]
Institut fur Organische Chemie
der Universitat-Gesamthochschule Paderborn (FRG)
Nucleotide Analogues as Antiviral Agents. (ACS Symposium
Series, Vol. 401). Edited by J. C. Martin. American Chemical Society, Washington, DC (USA) 1989. viii, 190 pp.,
hard cover, $53.95.--ISBN 0-8412-1659-2
This book is a collection of papers presented at a symposium held on the occasion of the 196th meeting of the American Chemical Society in September 1988. As the editor notes
in his introduction, efforts to develop antiviral nucleoside
and nucleotide analogues as an answer to the AIDS epidemic
have been greatly increased in the last few years. The majority of the nucleoside analogues used up to now, of which
3‘-azidothymidine and 9-(hydroxyethoxymethy1)guanine
(Acyclovir) are the two most important, are effective in the
form of 5’-triphosphates. The phosphorylation proceeds via
three steps, one of which is often a bottleneck-for example,
in the case of azidothymidine this is the phosphorylation of
the 5‘-monophosphate to the diphosphate. Thus it already
became apparent some time ago that, instead of nucleoside
analogues, one might try to introduce nucleotide analogues
with potential antiviral activity into the cells. Since one of the
obstacles to the uptake of nucleotides is that they can be
broken down by enzymes in the plasma membrane, phosphate analogues that cannot be broken down in this way
seem to offer especially good chances for successful uptake.
Consequently several chapters of the book are mainly concerned with results obtained using the stable phosphonate
derivatives. In addition, however, there are separate chapters dealing with other derivatives, e.g. with nucleoside-5’amines and -acetamides (Chapter 7), nucleoside-5’-sulfamates (Chapter 9), nucleotide dimers (Chapter 11) and
oligonucleotides (Chapter 12).
As the book is a collection of articles by different authors,
the quality of the contributions varies. For example, some
contain unnecessarily extensive tables (pp. 10, 57,60,61 and
67) which make it difficult for the reader to distinguish essentials from non-essentials. Also very often the absence of compound names under their structural formulas-where these
are given-is confusing, as it makes it difficult to quickly
relate them to the text. The book is evidently intended for
experts, for whom the meanings of the many abbreviations
are obvious, and who will know, for example, that DHPG,
0 VCH Verlagsgesellschaft
mbH. 0-6940 Weinheim, 1990
which incidentally does not appear in the index, is identical
to Ganciclovir. As is often the case in symposium proceedings, every article stands alone and no account is taken of
other articles with which there is an overlap of subject matter
or an amplification of a topic, as, for example, in contributions 4 and 5 which deal with the compounds 9-(2-phosphony1methoxy)ethyladenine (PMEA) and 9-(2-phosphony1methoxy)ethylguanine (PMEG). No doubt in order to
produce this symposium volume as cheaply as possible, the
text is very closely printed throughout, and this has not exactly made the book user-friendly. Also it seems a little
strange that in the index entries referring to azidothymidine
are found not only under this abbreviated name but also
under “3‘-azido-2’,3’-dideoxythymidine”.
In addition to the more general discussions the book contains a few items of information which I found especially
interesting, not least because they could provide a stimulus
for future experiments. For example, it is remarked on pages
80 and 85 that phosphonate derivatives often show higher in
vivo than in vitro activity. Unfortunately no further commentary on this is given. Another interesting result reported but
not explained further is that some phosphonate alkyl esters
also show antiviral activity (p. 32).
This book is the first of its kind on antiviral nucleotide
analogues. Although none of the compounds discussed here
has yet been cleared for clinical use, it becomes evident from
reading the book that this is a class of compounds with great
potential, and that further systematic research on these is
justified. Despite the shortcomings mentioned, the book provides a good basis of material for the specialist.
Fritz Eckstein [NB 1053 IE]
Max-Planck-Institut fur Experimentelle Medizin,
Gottingen (FRG)
Nitration. Methods and Mechanisms (Organic Nitro Chemistry Series). By G. A. Olah, R. Malhotra, and S. C. Narang.
VCH Verlagsgesellschaft, Weinheim, VCH Publishers,
New York 1989. xii, 330 pp., hard cover, DM 145.00.ISBN 3-527-26698-410439573-144-4
The third volume to appear in the Organic Nitro Chemistry Series, this book deals exclusively with aspects of nitration in organic chemistry. In keeping with the preceding two
volumes (Nitrazoles and Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis), it provides a broad survey of
the subject, encompassing in four chapters many of the
methods and mechanisms for the nitration of aromatic and
aliphatic compounds.
After a brief introduction in Chapter 1 (8 pages, 21 literature citations), the authors go on in Chapter 2 (108 pages,
264 literature citations) to describe preparative methods for
aromatic nitration. Numerous examples of the great many
reagents used for nitrating arenes appear mainly in tabular
form, accompanied in the text by the corresponding methods.
The authors have devoted a great deal of space in one
section of Chapter 2 to nitration with nitronium ions; unfortunately, the examples in this section are not as complete as
those from the section on nitration with nitric-sulfuric acid
(isomer-distribution data). Although this format does not
allow for comparison of aromatic nitration methods by way
of example, it gives the reader a good, comprehensive
overview. Some neglect is also apparent in the cursory treatment of homolytic (i.e., free-radical) and, more importantly,
nucleophilic nitration, considering the significance of these
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Angew. Chem. Int. Ed. Engl. 29 (1990) No. 7
topics. One other disturbing feature of this chapter is the
citation of patents in the reference section with no reference
to the appropriate Chem. Abstr. Citation.
Chapter 3 (101 pages, 160 literature citations) is divided
into three sections, covering mechanisms for electrophilic,
free radical, and nucleophilic nitration of arenes. These fully
detailed sections provide insight into the current level of
understanding of nitration mechanisms. As in Chapter 2,
however, the discussion of nucleophilic nitration is somewhat short (2 pages) compared to the coverage of electrophilic nitration.
In Chapter 4 (92 pages, 269 literature citations) the nitration of aliphatic compounds is surveyed. Here again, wellarranged examples accompany the text. The book ends with
author and subject indexes that leave no stone unturned.
At this high price, one would have expected better-quality
structural formulas. Nevertheless, this third volume of the
series on nitro compounds, like its predecessors, merits recommendation.
Thomas Ziegler WB 1060 IE]
Institut fur Organische Chemie
Biochemie und Isotopenforschung
der Universitat Stuttgart (FRG)
Symmetrien der Natur. Ein Handbuch der Natur- und Wissenschaftsphilosophie. By K . Mainzer. De Gruyter, Berlin
1988. 739 pp., hard cover, DM 365.00.-ISBN
3-1101 1507-7
Most important are those areas of pure science in which there
is no longer a mention ofpractical applications, but where pure
thought investigates the hidden harmonies of the universe. This
inner circle, where one can hardly distinguish between science
and art, is perhaps the only place where humanity today is
confronted with pure truth, that is no longer veiled by human
ideoiogy and desires.
W Heisenberg
Among his contemporaries in the development of the
“new physics” during the early decades of this century, it was
particularly u! Heisenberg who pointed out the fundamental
importance to physics of abstract symmetry (i.e. symmetry in
a general sense, not only geometrical). This importance is
now universally accepted, and is part of the common knowledge of every young physicist and chemist. Furthermore, we
now regard symmetry as providing a fascinating link between very different fields of human thought and knowledge.
There have thus been many minor and major attempts to
treat this subject in book form.
This book by Klaus Mainzer occupies a special position in
view of its comprehensiveness, exemplary depth, and thoroughness. In the words of the subtitle, it is in fact a “handbook on natural philosophy and science”. In over 700 pages
it treats, or at least touches on, almost every aspect of this
theme. Its five chapters are arranged as follows: 1. The early
history of symmetry; 2. Symmetry properties in modern
mathematics; 3. Symmetry properties in classical physics
and natural philosophy; 4. Symmetry properties in modem
physics and science; 5. Symmetry and philosophy (also art
and architecture). The book also includes a comprehensive
bibliography and index, which serve as an encyclopedic
guide to specific topics, specific facts, people, and historical
aspects. It would be useful to enlarge the index in future
editions so as to increase still further the value of the book
as an “encyclopedia of symmetry”.
Angew. Chem. I n l . Ed. Engl. 29 (1990) No. 7
It would not be appropriate in this short review to try to
summarize the contents of this comprehensive work. The
book combines many functions, being at the same time an
encyclopedia, a textbook and an intellectually stimulating
entertainment. There is scarcely a single aspect of the subject
on which one fails to find a chapter, or at least a brief comment with literature references. Whole chapters of the book
can be used by the student who needs an “introduction to
symmetry for chemists” (or for physicists, mathematicians
etc.). Perhaps the most remarkable comment I can offer is
that, in avoiding the effort of “textbook-reading” I have
read many of the book’s 700 pages for pleasure and relaxation and was never bored. This is literary writing for scientists in the best possible sense.
Let us cite two sentences from the introduction to
Mainzer’s book: “In the end, therefore, there remains the
need to achieve an understanding of nature which will enable
Man to act in harmony with nature, even more so because of
his scientific knowledge and technological capabilities. For
this reason the traditional approach of the philosophy of
nature, which views research as part of human history and
nature, is becoming again an important component of a
scientific education”.
“Symmetrien der Natur” could and should be used as a
textbook of general scientific education by all science students, and is also basically suitable for students of the philosophically orientated humanities. Regrettably, the very high
price, which is only partly justified by the excellent quality of
production and presentation, is likely to prove an obstacle to
this readership. One can therefore only hope that “Symmetrien der Natur” will achieve enough sales to persuade the
publishers soon to bring out a second edition at a lower
price. Meanwhile, I recommend to all who can afford it to
buy the book. They will not regret it.
Martin Quack [NB 1055 IE]
Laboratorium fur Physikalische Chemie
der Eidgenossischen Technischen Hochschule,
Zurich (Switzerland)
Patai’s Guide to the Chemistry of Functional Groups. By
S. Patai. Wiley, Chichester 1989. 455 pp., hard cover,
f. 24.95.-ISBN 0-471-91256-2
In the well-known series “The Chemistry of Functional
Groups”, 40 titles were published up to the end of 1988,
comprising 59 volumes with over 700 chapters and more
than 43 000 closely printed pages. In the book reviewed here
the series editor S. Patai has set out to provide an overall
picture of this impressive amount of material, to accompany
the immense stack of volumes that he has edited. So as to
make the information contained in this monumental series
more readily accessible, Patai has taken up a suggestion by
H. C. Brown, providing a 455-page summary of the entire
work with a detailed description of what the volumes contain.
The contents of the individual chapters are here described,
including important information such as the number of
pages, number of literature citations and the period that they
cover, and the nature of the tables, formula schemes etc. that
are included. This goes far beyond a mere summary of the list
of contents for each volume; Patai also summarizes the most
important chemical results, supported by many formulas. As
well as the author and subject indexes he also includes two
very useful sorts of cross-references: “complementary”
cross-references, which refer to descriptions of the same
VeriagsgeseiischaftmbH. 0-6940 Weinheim. 1990
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