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Book Review Chemistry of Acetylenes. By H. G. Viehe

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which it acts either as an electron acceptor or an electrophile. Typical examples are those given in the accompanying scheme.
Other examples mentioned are Beckmann rearrangements
and rearrangements of epoxides into ketones. [Recent
Developments in Organic Synthesis in Liquid Sulfur Dioxide. Synthesis 1971,639-645 ;56 references]
hydroxy compounds, sulfinic acids, thioles, amines, NH
acidic compounds, organophosphorus compounds, Grignard reagents, active methylene- and methine compounds,
aromatics, phenols, and N,N-dialkylanilines. Bis(sulfeny1
chlorides) such as (I), a-chlorocarbonylsulfenyl chlorides
[Rd 471 IE -MI
The stereochemistry of cobalt complexes with flexible tetradentate ligands is the subject of a review by G. R. Brubaker,
D. P . Schaefer, 3. H . Worrell, and 3. I . Legg. The ligands
treated are tetraamines and dithiadiamines with their donor
atoms located in a straight chain, and ethylenediamine-N,l
diacetate. The preparation of stereoisomers and the determination of their configurations, especially by the measurement of circular dichroism or optical rotatory dispersion, are described in detail. The importance of cobalt
complexes of these ligands is due to their comparatively
high kinetic stability against substitution reactions ; it is
conceivable, therefore, that knowledge gained from the
study of cobalt complexes can be used for the determination of configurations of other transition metal complexes
which cannot be isolated readily. [Complexes of Cobalt(II1)
with Flexible Tetradentate Ligands. Coord. Chem. Rev. 7,
161-195 (1971); 102 references, 8 figures, 10 tables]
[Rd 477 IE -HI
Substitution and cyclization reactions of suifenyl halides are
treated comprehensively in a review by E. Kukle. The main
substitution reactions dealt with are the sulfenylations of
such as (2), and substituted chloromethanesulfenyl chlorides such as (3) undergo cyclization reactions. Experimental details are given for individual reactions. [One Hundred
Years of Sulfenic Acid Chemistry. Substitution and Cyclization Reactions of Sulfenyl Halides. Synthesis 1971, 617 to
638 ; 325 references]
[Rd 470 IE -MI
Titrationen in nichtwassrigen Medien (Titrations in Nonaqueous Media). By I. Gyenes. Ferdinand Enke Verlag,
Stuttgart 1970. 701 pp., 206 figs., 108 tables, DM 84.-.
The book opens with an exposition of the various acidbase theories, together with discussions on the problems of
acid and base strength and its dependence on the nature
of the solvent. This gives a basis on which the processes
occurring during titrations in nonaqueous media may be
explained (120 pages). Some 70 pages are devoted to the
solvents themselves, with particular reference to their
properties, their behavior, and their purification; the
titrants concerned, both acidic and basic, are dealt with
in 35 pages or so.
End-point determination in titrations takes 140 pages.
Descriptions are given of visual and photometric methods
using color indicators, and also instrumental methods
such as potentiometry, conductometry, oscillometry, voltametry, amperometry, and thermometry. In each case
particular attention is paid to examples of application,
withont going into the fundamentals of the method.
The titrations themselves occupy 250 pages. Details are
given of the determination of acidic substances, such as
acids, acid anhydrides, acyl, alkyl, and aralkyl halides,
enolic hydroxy and imide groups, phenolic and alcoholic
hydroxy groups, nitro compounds, and acid salts. In the
section on basic compounds, aliphatic, aromatic, and
cycloaliphatic nitrogen-containing compounds and their
salts are discussed. Methods are also given for the titration
of carbonyl groups, sulfur-containing compounds, and
This book has much of value to offer both to those concerned with theoretical aspects and those concerned with
practical aspects. The latter will find very many specific
analytical procedures and numerous useful tips. The book
can be warmly recommended to anyone concerned with
this subject area.
Giinther Kraft [NB 17 IE]
Chemistry of Acetylenes. By H. G. Viehe. Marcel Dekker
Inc., New York 1969, 1st edit., xv, 1298 pp., numerous
tables and formulas, bound, S 59.50.
This brilliantly successful book shows in clear and readily
comprehensible form the rich and diverse nature of acetyAngew. Chem. internat. Edit.
Vol. I 1 (1972) 1 No. 4
lene chemistry, and the extent to which acetylene derivatives
occur in many fields of organic chemistry. Though intended primarily for research workers and chemistry
students, it can also be used as a wide-ranging source of
information to stimulate new ideas and as an easily understandable introduction to the individual topics of acetylene
In the production of this book the author had the collaboration of 22 subject specialists from seven countries, and
many other scientists. They have succeeded in creating a
comprehensive survey of the chemistry of acetylene and
its derivatives, thereby meeting a long-felt need of organic
chemists. Topics not dealt with in detail in the text are
completely covered by the approximately 4150 literature
references, which contain practically all that is known
and is worth knowing about the chemistry and reactions
of acetylenes.
The book consists of 22 chapters, which deal with the
following individual themes: theoretical considerations on
the structure and physical properties of acetylenic compounds and the nature of the triple bond; preparation of
acetylenes and polyacetylenes by dehydrohalogenation
and other elimination reactions, and also by substitution
reactions, starting with acetylenic compounds; ionic additions to acetylenes;radical additions; partial hydrogenation
of acetylenes; rearrangement of alkynes to allenes; synthesis of cyclic and heterocyclic compounds by cycloaddition to acetylenes and cyclization reactions; coupling
of acetylenes; preparation of halogenated acetylenes,
alkynyl ethers and thioethers; ynamines; acetylene derivatives of elements of Groups 111b, IV, and V of the periodic
table; description of naturally occurring acetylenes; cyclic
acetylenes; dehydrobenzene and dehydrohetarenes.
In order to achieve the desired degree of completeness, the
book ought to contain a related section on the work
carried out by Reppe with acetylene under pressure and
a detailed description of Reppe’s discovery of the carbonylation of acetylenes. Some of these reactions are
carried out today on an industrial scale, and have led to such
valuable intermediates as acrylic acid and acrylic esters.
The topics concerned are certainly covered by the literature references, but their description in the text would be
an added boon for the reader.
Anyone concerned with the practical applications of acetylene chemistry should have this book close at hand.
It is therefore to be hoped that this book, which by reason of
its arrangement and its content is an irreplaceable reference
work for the whole field of acetylene chemistry, will
maintain its value in the future by revised editions, each of
which will need to be brought up to the current state of the
Nikolaus uon Kutepow
[NB 18 IE]
Milk Proteins. Chemistry and Molecular Biology. Vol. 1.
Edited by H . A. McKenzie. Academic Press, New YorkLondon 1970, 1st edit., xvii, 519 pp., numerous figs.,
bound, $28.50.
Only about a quarter of this book, the first of a two-volume
work, is devoted exclusively to milk proteins, and this
consists of a brief historical and a longer chemical survey,
which is also concerned with fractionation, nomenclature,
biosynthesis, and biological functions, together with an
extensive chapter on immunological studies. The main
part of the book is concerned with the general chemical
Angew. Chem. internat. Edit.
Vol. 11 (1972) No. 4
and physical methods of protein chemistry, and in particular with elemental analysis, the analysis of the functional
groups of the amino acid, peptide, and carbohydrate residues, chromatography and electrophoresis (with particular
regard to the interactions between the components of the
mixture to be analyzed), spectrophotometry, and the other
physical methods used to study changes in the degree of
association, conformation, and structure.
The basic problem here is whether there is much point in
describing general techniques in a book on specific substances. The answer in this case cannot be an unqualified
no, since most of the techniques are illustrated with
examples involving milk proteins, and in some (possibly
too few) cases there are discussions on the method most
applicable in the case in question. For the protein chemist,
most of the chapters could have been shortened or replaced
by references to appropriate monographs; however, the
worker who is only occwionally concerned with proteins
will welcome the explanations of the individual methods.
For complete information it will be necessary to refer also
to the second volume, which, according to the publisher’s
announcement, will deal with individual milk proteins
and also the casein micelles and rennin. If the second volume
matches the first in quality and attractive layout, this could
be the best and most detailed work on milk proteins. The
problems are discussed critically and precisely, and the
literature has been surveyed up to 1970. The work is
highly recommended.
H . G . Maier [NB 19 IE]
Lehrbuch der Pharmazeutischen Chemie (Textbook of
Pharmaceutical Chemistry). By H . Auterhofl, with the
collaboration of J . Knnbe, Wissenschaftliche Verlagsgesellschaft mbH, Stuttgart 1971. 6th, revised and
amplified edition, xii, 636 pp, 1 fold-out table, clothbound, DM 54.-.
This was the first German textbook of pharmaceutical
chemistry that attempted to present the fundamentals of
general inorganic and organic chemistry, in order to discuss
more thoroughly the chemistry of compounds relevant to
pharmaceutics, their analysis, and medical applications.
The success of this approach is shown by the otherwise
inexplicable fact that six editions of Auterhoff’s book have
appeared within eight years. At present, the work has no
rival. The present edition is arranged in the way that has
proved so satisfactory in the past. The inorganic section,
about 100 pages long, is arranged in accordance with the
periodic table. The organization of the organic chemistry
section presented considerable problems, and so a compromise has been arrived at; first of all the pharmaceuticals
from the simple and more complex chemical classes are
dealt with (e.g . hydrocarbons, alkyl halides, alcohols,
phenols, carboxylic acids, amines, proteins, carbohydrates,
steroids, alkaloids), followed by groups of pharmaceuticals
arranged by their pharmacological or therapeutic properties (e.g . analgesics, psychotropics, coronary dilators, hypnotics, antihypertensives, cytostatics, chemotherapeutics,
antibiotics, hormones, vitamins). This brief selection may
show how wide a range of compounds is covered.
The sixth edition has not only been amplified to bring it
as up to date as possible, but in addition some completely
new chapters have been added, e.g. on the absorption,
distribution, and biotransformation of pharmaceuticals
and on enzymatic analysis. Particular care has been taken
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