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Book Review Advances in Alicyclic Chemistry. Edited by H. Hart and G. J. Karabatsos

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ular structure and also gives some indication of the tensile
strength, stiffness, hardness, and modulus of elasticity. Polyethylenes are therefore expediently classified as being of low,
medium, or high density.
In the remaining five chapters the connections are investigated which exist between the structure of polyolefins and
their physical, chemical, electrical, and thermal properties
and their behavior on being processed. The last chapter is
particularly important for people interested in the technology
of plastics. Great emphasis is placed upon the relation between structure and rheology, the melt flow index being
stressed as a suitable parameter. When the molecular weight
distribution, which determines inter alia the shrinkability and
distortion tendency, is taken into account, the melt flow
index proves a good numerical indication of the workability,
as well as of the shock and breaking behavior of formed
objects. The progress which has been made in the extrusion
of polymers is alluded to and phenonema such as melt fracture are discussed.
Boenig’s book should appeal to both researchers and technologists. The fruitfulness of the cooperation of these two
groups of workers is evidenced by the spectacular advances
made in the field of polyolefins during the last decade. The
book may well make an important contribution to this continuing development.
The book is comprehensibly written, comprehensively subdivided, richly furnished with illustrations and tables, and
contains a wealth of references to the original literature.
H. Weber
[NB 624 IE]
Electrophilic Additions to Unsaturated Systems. By P . B. D .
de la Mare and R . Bolton. Reaction Mechanisms in Organic Chemistry, Monograph 4. Edited by C. Eaborn and
E. D. Hughes. Elsevier Publishing Company, AmsterdamLondon-New York 1966. 1st Edit., x, 284 pp., numerous
schemes and tables, Dfl. 40.00.
The present monograph, which is the fourth in the series
“Reaction Mechanisms in Organic Chemistry”, deals with
electrophilic additions to unsaturated systems. One of the
authors, Professor de la Mare, has himself made numerous
experimental contributions in this field.
The book is divided into 13 chapters. A short introduction
and a chapter on the chemistry of carbonium ions are followed by a discussion of the principal electrophilic additions.
These include hydration, the addition of weak acids, of
mineral acids, and of halogens, epoxidation, and the addition
of sulfenyl halides and of compounds containing electrophilic nitrogen, phosphorus, or arsenic. The final chapter
deals with electrophilic additions to acetylenes, allenes, conjugated dienes, and to other systems such as C=O, C = N ,
S=O, and N = N double bonds.
The content of the book, which is built up on a purely theoretical basis, is extremely rich; the literature is covered up to
the end of 1964.
No procedures are given for the execution of electrophilic
additions, nor are any to be expected in view of the very
concise presentation.
The book is very well written, and as a valuable contribution
to theoretical organic chemistry it makes a n excellent companion to the volumes published earlier.
F. Asinger
[NB 583 IE]
Introduction to Practical High Resolution Nuclear Magnetic
Resonance Spectroscopy. By D. Chapman and P. D. Magnus. Academic Press Inc., -London-New York 1966. 1st
Edit., ix, 112 pp.. 30 illustrations, numerous tables,
25 s/%4.25.
This book is intended to provide a first introduction to
nuclear magnetic resonance spectroscopy and its potentialities
244
for students and for chemists engaged in structure determinations of organic molecules; its particular aim is to
introduce them to carrying out these studies in practice. For
this reason the authors intentionally desist from any form
of theoretical derivation.
The fundamental ideas such as chemical shift and spin-spin
coupling are introduced in a few words and are clearly
explained by means of examples. Reference is made to
detailed monographs for deeper study. The section on
experimental technique is somewhat more expansive. The
use of 19F, 3LP, 14N, and 13C nuclear resonance in organic
structural analysis, and five well chosen examples, close the
first part.
The second part consists of 37 very clearly arranged tables
of T values and coupling constants from recent literature.
This book can be recommended as a brief introduction into
the methods and experimental technique, and into the
analysis of spectra, for chemists who wish to use nuclear
resonance spectroscopy for determination of structure.
H . Friebclin
[NB 665 lE]
Advances in Alicyclic Chemistry. Edited by H. Hart and G. J.
Karabatsos. Academic Press Inc., London-New York 1966.
1st Edit., x, 395 pp.. numerous illustrations and tables,
bound $ 16.50.
This book is the first volume of a new series in which it is
intended regularly to report the most recent results in the
chemistry of alicyclic compounds. The reviewer agrees with
the editors that the explosive growth of the original literature
justifies a further new series.
The editors have been successful in obtaining for this volume
competent authors who in their own papers have contributed
important material to the fields which they treat here. Considered as a whole, the book provides a balanced and in
parts highly critical survey.
J. Meinwuld and Y. C. Meinwald report on bicyclo[n.l.l]alkanes and related tricyclic systems. It would be welcomed
by the reviewer if the nomenclature rules for bicyclic and tricyclic bridged compounds given by the authors in their
introduction were generally adopted. The main discussion of
the bicyclic compounds is devoted to the bicyclo[2.1 .l]hexane
and the bicyclo[l.l.l]pentane system, their syntheses and
reactions, and rearrangements of their derivatives. A special
section is devoted to consideration of highly strained tricyclic
compounds (tricyclopentane, -hexane, and -octane).
The chemistry of cyclopropenes is surveyed by G.L.Closs. H e
discusses in detail, not only the synthetic possibilities for
cyclopropene and its derivatives, but also their reactions, the
spectral properties, and the bonding. The peculiar “aromatic” properties of the cyclopropenyl cations and of the
cyclopropenones are treated in depth.
A detailed chapter (A. J. Waring) is devoted to cyclohexadienones. The author brings together the extensive and
widely scattered material with great care. Of the 121 pages
of this chapter, 53 pages are reserved for the varied ways of
forming cyclohexadienones; other parts describe their transformations and reactions. A special section is reserved for the
photochemistry of cyclohexadienones.
In the next chapter K . F. Koch surveys the photochemical
rearrangements of monocyclic tropolones and benzotropolones, and of colchicine and isocolchicine. The structures
of the “1umi”-products are discussed in detail with reference
to their UV, IR, and N M R spectra.
I n spite of two previous reviews of “reactions at a bridgehead” 111, the chapter by R. C. Fort and P. v. R . Schleyer on
the same theme contains much new experimental material
that has become available only during the last five years.
Besides containing a theoretical section, this chapter collects
[l] D. E. Applequist and J. D . Roberts, Chern. Reviews, 54, 1065
(1954); U.Schollkopf, Angzw. Chem. 72, 147 (1960).
Angew. Chem. internat. Edit. I VoI. 7 (1968) 1 No. 3
together the reactions of bridgehead carbenium ions, carbanions, and free radicals.
One can only hope that the same high level will be maintained
in the further volumes planned for this series. The editors
and authors will then have given us a good “Advances”
M. Hannck
[NB 668 IE]
series.
High Resolution Nuclear Magnetic Resonance Spectroscopy.
By J . W . Emsley, J . Feeney, and L. H . Sutcliffe.Pergamon
Press, Oxford 1965 and 1966. 1st Edit., 2 volumes, xxiii,
1154 pp.. numerous illustrations and tables, linen 105 s.
The two volumes of this work begin with a detailed description of the physical principles underlying N M R techniques,
which is followed by two chapters (together 79 pp.) on the
calculation of chemical shifts and coupling constants in
accord with various theories. The individual parts of a
spectrometer are described for the experimentalist, as are
the practical methods of preparing the sample, of standardization, and of the actual measurement; information o n these
subjects had previously to be searched out from different
sources and supplemented by personal experience. The chapter
o n spectral analysis, i.e. o n determination of 6- and J-values
from measured spectra occupies 200 pages, which constitute
almost a third of volume 1. The theory is used to develop
expressions needed for the analysis of all the important spin
systems and gives indications for their evaluation. Spectroscopic effects of chemical equilibria and fast reactions are
placed in a special chapter.
The whole of volume 2 is devoted to special applications of
the method to chemical problems, the voluminous material
being arranged according to the atomic nuclei under study
(IH 205 pp., 19F 97 pp., other nuclei 139 pp.) and within
each such section according to the chemical classes of
compounds. Although the literature has not been completely
covered up to 1963, this collection of material, with its many
clear tables, is a n imposing performance by the authors. It is
a pity that two whole years passed before publication of this
work! The appendix to the book must also be recognized as
very useful; it contains, inter nliu, the contributions of a
benzene ring to the shielding of a neighboring proton
(according to Johnson and Bovey) and Tiers’ tables of T values
which were hitherto of limited availability.
The work reviews mainly the results and opinions in the
original papers and generally refrains from new interpretations
of the material reported. Evaluations, if made at all, are
expressed in very restrained language; for instance one does
not read “The authors’ measurements are valueless” but,
instead, “It is difficult to assess the theoretical significance
of their measurements”.
The opportunity to unify definitions, terms, and symbols has
not been exploited; o n the contrary, the usage, e.g. for
chemical shift, for line width, or for mean lifetime, changes
according to what was used in the paper being reviewed. Some
equations in volume 1 (particularly on pages 481 to 491)
contain errors which can mislead the user; and in these
places the conscientious reader may need many hours to
recognize errors as such.
Naturally it is not difficult, with a work of this range, to find
items that have been incompletely or incorrectly described,
particularly as this is a field of study that touches on a series
of different scientific disciplines - from theoretical physics to
the chemistry of natural products. Thus no author - and
also n o reviewer - will be able to master the whole of the
material. All the greater, therefore, is it to the authors’ credit
that they have provided a comprehensive book. It is not
conceived as a n introduction to the method; but it can be
recommended to every N M R spectroscopist for advanced,
critical study. Further, these volumes are likely to be essential
to everyone as a reference work; for this purpose they may be
considered as a new edition of Pople, Schneider, and Bernstein’s standard work that appeared in 1959.
A . Munnschreck [NB 671 IE]
Angew. Chem. internat. Edit.
Vol. 7 (1968) J No. 3
Indole Alkaloids. An Introduction to the Enamine Chemistry
of Natural Products. By W. I . Taylor. Vol. XXVIII of the
series: A Course in Organic Chemistry, Advanced Section.
Pergamon Press, Oxford 1966. 1st Edit., 148 pp., numerous
figures, paper back 25;-.
On 140 pocket-book pages, half of which are filled with
structural formulae, an attempt is made to treat the chemistry
of the indole alkaloids unconventionally deductively by
emphasizing the reactions of the indole system and biogenetic
considerations. This method, the fulfilment of which has
become possible only as a result of the rich volume of data
collected during the last 10 years (the principle is due to Sir
Robert Robinson) assures the reader of continuity, while the
individual facts d o not appear overwhelming. In his search
for (generally biogenetic) inter-relationships the author has
not hesitated to formulate hypothetical intermediate stages
and as yet undiscovered alkaloid variants. Occasionally
more remote analogies are resorted to in order to explain
the course of reactions (e.g. Lycorine-neostrychnine on p.79).
By adhering to this method the author succeeds in including,
although sometimes only briefly, a large number of preparative
and physicochemical details.
As a result of its recent date of publication, and the concepts
that are consequently involved, the book is somewhat more
modern than other works on alkaloids. Numerous results of
the last few years appear to have been summarized here
for the first time. Entries such as picraline, echitamine,
copsine, vindoline, vincamine, voacamine, schizozygine,
burnamicine, and also skytanthine as a mevalonoid nonindole
alkaloid, characterize part of the developments revealed by
the author. In general, the biogenetic postulates are based o n
mevalonic acid, although at the time of writing the book no
confirmatory labeling experiments had been carried out.
Although the book could be recommended as a summary, or
to those who wish to gain a brief overall picture of the more
recent classes of alkaloids, a certain degree of familiarity is
taken for granted. Compared with the books by Bentley, Boit,
or Manske-Holmes, it is not really suitable as a n introduction. The formulas are well presented, misprints are rare,
and the price is not unreasonable. H...J . Teuber [NB 637 IE]
Treatise on Analytical Chemistry. Edited by I. M. Koithoff
and P . J. Efving. Part 11, Vol. 4: Analytical Chemistry of
Inorganic and Organic Compounds. Interscience Publishers, a Division of John Wiley and Sons, New York-London-Sydney 1966. Part 11, Vol. 13: Analytical Chemistry
of Inorganic and Organic Compounds. 1st Edit., xxi,
528 pp., 14 illustrations, 29 tables, bound 160 s.
Two very different volumes of KoZthof and Elving’s Handbook of Analytical Chemistry are now available for review,
Volume 4 of Part I1 of this work [*I deals with the analysis of
the elements silver (E. P . Przybylowicz and C . W. ZuehZke),
gold ( N . Herz), calcium ( K . K . Turekian and E. Bolter), strontium and barium ( K . K.Turekian and E. Bolter), radon and
radium (J. Sedlet), and aluminum (G. H . Fnrrah and M. L.
Moss). This volume, like its predecessors, is written by
experts in the analysis of the elements that they treat, and it
is in line with the usual careful work that is known from
previous volumes.
Volume 13 deals with the determination of functional groups
in organic compounds. The two preceding volumes 11 and 12
dealt with methods of elemental analysis of organic compounds, i.e. the determination of carbon, hydrogen, nitrogen,
phosphorus, oxygen, sulfur, the halogens, boron, silicon, etc.
The present volume describes the analytical methods used
for determining functional groups in organic compounds, i.e.
typical structural features that can be used for characterization or for quantitative determination of organic compounds.
Chemical and physical methods (IR, UV, Raman, N M R , and
mass spectrometry, as well as chromatographic methods of
[*I Cf. Angew. Chem.
76, 139 (1963).
245
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