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Book Review Atlas of Stereochemistry. Absolute Configurations of Organic Molecules. By W. Klyne and J. Buckingham

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Elektroorganische Chemie (Electro-Organic Chemistry). By F.
Beck. Verlag Chemie, GmbH, Weinheim 1974, 1st Edit.,
xvi, 391 pp., 76 figs., 47 tables, bound, D M 88.-.
The author has been completely successful in his aim of
presenting this diversified and important boundary area in
detail and from a modern point of view. The book stands
out clearly from the current flood of monographs about the
subject by virtue of its clarity, balance, and adherence to
actual practice.
Chapter 1 begins with a brief introduction to the layer
model of the electrode/electrolyte phase boundary and to
electrode reaction mechanisms (initiation, subsequent reactions, reactive intermediates). The technological advantages
of electrosynthesis (control of the products formed, avoidance
of co-products) are demonstrated and documented by impressive data from industry. Chapter 2 provides a clear treatment
of the important relationships between the potential, current
density, concentration, and time (cyclic voltametry, polarography, rotating disk electrodes). The electroanalytical criteria
for electrode mechanisms are collected in tables for rapid
access. The bibliography lacks only literature references to
low-temperature electrolysis [Reilley, Anal. Chem. 44, 142
(1972)l and to recent developments of the combination of
electrochemistry with ESR spectroscopy [Bard, J. Phys. Chem.
75,3281 (1971)l. Chapter 3, keeping close to practice, characterizes the cell components (in some cases even giving their
suppliers), and the cell and electrolyte types. The description
of measuring techniques and electronics is somewhat too brief.
Chapter 4 is the longest section and constitutes the core
of the book (140 pages). Here, supplied with 1050 references,
some from the patent literature, are described the important
possibilities of synthesis, both at the cathode and anode,
arranged by classes of compounds. The author finds a good
compromise between a strict review presentation (reactions
with conditions and yields, mechanistic investigations, industrial data) and the most detailed information. There are
detailed treatments of: cathodic hydrogenation of multiple
bonds (C=C, C=O, C=N, N=O), cathodic fission (C-Hal,
onium ions), anodic oxidation (olefins, aromatic compounds,
carboxylic acids, amines), cathodic couplings (activated olefins,
carbonyl compounds), anodic couplings (Kolbe electrolysis,
aromatic compounds, olefins), electrochemical substitutions,
cyclizations, and polymerizations. Chapter 5 gives a brief and
stimulating introduction to nonpreparative aspects such as
electrochemical production and storage of energy (fuel cells,
batteries), surface techniques (electrocoating, corrosion protection), and material separation (dialysis, waste water purification).
Relevant illustrations and carefully thought out formula
schemes everywhere aid understanding of difficult material,
and reinforce visually the access to information. Extensive
subject and author indexes make it possible to find rapidly
any desired fact. The printing and the production are immaculate.
The book can be unreservedly recommended to all who
wish to occupy themselves or are already engaged in this
field, as an introduction and as a comprehensive source of
information.
H . J . Schujier [NB 260 IE]
Atlas of Stereochemistry. Absolute Configurations of Organic
Molecules. By W Klyne and J . Buckingham. Chapman and
Hall, London 1974. 1st Edit., xvi. 311 pp., bound E 15.00.
This is the first of three attempts known to the reviewer
to publish systematic compilations of the absolute configurations of optically active substances. In it the authors have
assembled 3000 compounds in 21 1 full-page tables, for which
they concentrated on molecules containing one or two centers
Angevr. Chrm. internal. Edit.
/ Vol. 1 4 ( 1 9 7 5 ) 1 N o . 6
of chirality and on selected representatives of the more important classes of natural products. Metal complexes (except for a
few metallocenes) and polymers were not included; on the
other hand it is very good to see tables of compounds that owe
their optical activity to isotopic labeling, a chiral heteroatom
(e.g. S, P, or Si) or axes or planes of chirality. The literature
is covered up to the end of 1971.
Compounds that have been correlated chemically or spectroscopically with one another are always represented on
the same page by their stereoformulas; when possible and
essential, the sign of a,,and the specification by the ( R / S ) nomenclature in the name are included. Formulas of compounds whose absolute configuration has been determined
by the Bijvoet method are marked in special manner. By
this method of arrangement the extensive atlas remains very
clearly set out in spite of the great wealth of material. Occasionally general rules are added (e.g. about the correct way
to “read” Fischer projections), or information about review
literature. The book closes with formula, author, and subject
indexes; these are not wholly free from error.
Everyone concerned with questions of absolute configuration must recognize the enormous amount of work that has
gone into the preparation of such an atlas and treasure the
resu1t:Searching the literature of optically active natural products is generally easy, as in most cases only one enantiomer
occurs in nature; in contrast, for synthetic compounds and
degradation products it is often very time-consuming to track
down the sources for a correct assignment of the absolute
configuration, and here the atlas offers particularly welcome
assistance since the relation to examples with truly unambiguously known stereochemistry can be recognized at a glance.
A few blemishes do not spoil the good total impression
(the reviewer sought and found, for instance, faulty citation
of authors’ names. missing notes, and missing substituents
on formulas; for A45.14 there is a prochirality center
specified as a chirality center; chaetocin is reproduced
by a formula that contains a mirror plane-as does the original
paper). This book can be recommended to all who may need
to find information rapidly about absolute configuration, and
it is likely to become soon a n essential part of the libraries
in the pharmaceutical industry as increasing attention is paid
to the differing activities of enantiomers.
Giinther Snatzke
[NB 265 IE]
Colorimetric Chemical Analytical Methods. By L. C . Thomas
and G. J . Chamberlin. The Tintometer Ltd., Salisbury 1974.
8th Edit., xli, 626 pp., bound, D M 130.-.
Photobiologie, Band 1: F’hysikalische Grundlagen. By R. K .
Cluyton. Vol. 33 of the series “taschentext“. Verlag Chemiei
Physik Verlag, Weinheim 1975. 131 pp., stitched, DM 16.80.
Digitale Elektronik. Grundlagen und Praxis. Eine Einfuhrung
fur Naturwissenschaftler. By G. Durcansky. Physik Verlag
GmbH, Weinheim 1975. xii, 217 pp., bound, D M 58.-.
441
Organometallic Chemistry, Vol. 3. Senior Reporters : E. W
Abel and F. G. A. Stone. The Chemical Society, London
1975. xx, 487 pp., bound, f 17.50.-A volume in the series
“Specialist Periodical Reports”.
Approaches to Camptothecin. By E. Winterfeldt/The Pyrrolizidine Alkaloids. By A. Kla’sek and 0. WeinbergovdlAdvances
in the Chemistry of Glycosaminides. By A. Ya. Khorlin and
S. E. Zurabyan. Vol. VI of the series “Recent Developments
in the Chemistry of Natural Carbon Compounds”. Edited
by R. Bogna‘r, V Bruckner, and Cs. Szdntay. Akademiai
Kiad6, Budapest 1975. 198 pp., bound, DM 29.-.
Advances in Inorganic Chemistry and Radiochemistry, Vol.
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Comprehensive Biochemistry. Edited by M. Florkin and E.
H. Stotz. Vol. 31: A History of Biochemistry. Part 111:
History of the Identification of the Sources of Free Energy
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Catalysis Reviews. Science and Engineering, Vol. 10. Edited
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Forscher zwischen Wissen und Gewissen. Edited by F. Cramer.
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Amino-acids, Peptides, and Proteins, Vol. 6. Senior Reporter:
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Mass Spectrometry, Vol. 3. Senior Reporter: R. A . W. Jolmsfone. The Chemical Society, London 1975. xiii, 402 pp..
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Lehrprogramm Chemie 11. By J. Nentwig, M. Kreuder, and
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General Chemistry. Principles and Structure. By J . E. Brady
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Creativity in Organic Synthesis, Vol. 1. By J. S. Bindra and
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Einfuhrung in die Molekiilsymmetrie. Ein Lehrprogramm fur
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Introduction to Chemistry. By 7: R. Dickson. John Wiley &
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Pyridine and its Derivatives, Supplement Part 4. Edited by
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Water and Aqueous Solutions. Introduction to a Molecular
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International Conference on Modern Trends in Activation Analysis. Edited by 7: Braun and E. Bujdosd. Reprinted from
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Organic Syntheses via Boranes. By H. C. Brown. With Techniques by G. W Kramer, A. B. Levy, and M. Mark Midland.
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f 9.45.
Foreign Compound Metabolism in Mammals, Vol. 3. Senior
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Soil Biochemistry, Vol. 3. Edited by E. A. Paul and A. D.
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Analysis of Silicones. Edited by A. L. Smith. From the series
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Chemical Applications of Pattern Recognition. By P . C. Jurs
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Developments in Biological Standardization, Vol. 27: International Symposium on Purity of Human Plasma Proteins
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g 11.OO.-A volume of the series “Specialist Periodical
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Trosr and L . S. Melvin, Jr., Vol. 31 of the series “Organic
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Immobilized Enzymes in Food and Microbial Processes. Edited
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Transport Phenomena. By W J . Beck and K . M . K . Muttzall.
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Topics in Nonbenzenoid Aromatic Chemistry. Edited by 7:
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Technique of Electroorganic Synthesis. Edited by N . L. Weinberg. Vol. V, Part I1 of the series “Techniques of Chemistry”.
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