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Book Review Ullmans Encyclopdie der technischen Chemie. Edited by E. Bartholom E. Biekert H. Hellmann H. Ley (deceased) W. M. Wiegert (deceased) and E

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Table I . Acyl cyanides 2 from acyl iodides 1 and CuCN.
a n-C,H,,
d (CH2)?CH
e PhCH:
85 Icl
59 141
Ref. Yield
82 [Icl
in one batch. After being refluxed for 1-2 h, the mixture
was filtered from Cut, and CH2CI2was removed at 0-5 "C.
Kugelrohr distillation gave 2d (420 mg, 62%)l4].
Method B: 2e: A suspension of CuCN (1.2 g, 13 mmol)
in anhydrous acetonitrile (100 mL) was warmed to 4060°C and le"' (2.5 g, 10 mmol) was added in one batch:
after 2-3 min a yellow, almost clear solution resulted. The
solution was stirred for I h, and the acetonitrile was removed using a rotary evaporator. The product was dissolved in CHzCIzand Cul filtered off. After evaporation of
CH2C12 the residue was distilled twice (Kugelrohr, b. p.
100-120°C/3 torr) giving pure 2e (730 mg, 50%)[51.
[a] Yields were not optimized. [b] 2,7-Dioxo-octanedinitrile. [cl Crude yield;
F. Asinger, A. Saus, H. Offermanns, H. D. Hahn, Jusrus Liebigs Ann. Cbem.
691 (1966) 92.
Received: June 9, 1981
supplemented: December 2, 1981 [Z 961 b I€]
German version: Angew. Cbem. 94 (1982) 80
prepared by the convential procedure["'. Similarly, a,p-unsaturated acyl cyanides such as 3,4-dimethyI-2-oxo-3-pentenenitrile have been obtainedf3];hereby, the olefinic double bond tends to shift out of conjugation under more forcing conditions.
Acyl cyanides 2 can also be rapidly prepared under mild
conditions in a one-pot procedure starting from acyl chlorides, CuCN, and iodide ion"'.
Experimenlal Procedure
All reactions are carried out under an atmosphere of N2,
because acyl iodides 1 (X = I) are easily oxidized.
Method A : 2d: CuCN (1.2 g, 13 mmol) was gently refluxed in CH2CI2(I5 mL) and Id (1.4 g, 7. I mmol) added
[ I ] a) S. Hiinig, Angew. Cbem. 94 (1982) I ; Angew. Cbem. lni. Ed. Engl. 21
(1982) 36; J. Thesing, D. Witzel, A. Brehm, Angew. Cbem. 6 8 (1956) 425;
P. Kurtz in Houben-Weyl: Meiboden der Urgonircben Chemie. Vol. 8,
Thieme. Stuttgart 1952, p. 304: b) K. Findeisen, DOS 2614240, 2614242
(1977): K. Findeisen, H. Schwarz, DOS2614241 (1977); K. Findeisen. W.
Draber, H. Schwarz, DOS 252821 I (1977): K. Findeisen. K. H. Linker,
DOS 2820575 (1979), Bayer AG; c) H. Klenk, H. Offermanns, W.
Schwarze, DOS 2708 182, 2708 183 (1978), Degussa.
121 H. M. R. Hoffmann, K. Haase, Synthesis 1981. 715.
[3] K. Haase, A. Weber, unpublished results.
14) E. Zbiral, L. Fenz, Monaish. Cbem. 96 (1965) 1983.
IS] 2e: IR (CCI,) 2220 (m), 1720 (vs). 1495 (m), 1455 (m), 1210 (m).1055 (s),
715 1s) cm '_ ' H - N M R (60 MHz, CDCI,) 6=4.0 (s, 2H), 7.3-7.5 (m,
5H). "C-NMR (CDCI,) 6=50.8 (C-3), 113.1 (C-I), 128.6, 129.1, 129.2,
130.0 (aromat.), 174.4 (C-2).
Nucleotide Analogs. Synthesis and Biological Function. By
K . H. Scheit. John Wiley & Sons, New York 1980. xi,
288 pp., price E 16.00.
The importance of nucleotides in biological processes
has led to intense preoccupation with this class of natural
substances. The base, sugar and phosphate portions are
modified for a variety of purposes. One reason for the synthesis of nucleotide analogs is doubtless to use them in obtaining information about nucleotide metabolism and
about the expression and replication of genetic information. Another driving force is the hope that once the mechanisms of expression and replication are known, nucleotide analogs may be designed for general use as chemotherapeutics, for example as interferon inducers or antiviral agents. A wealth of literature difficult to grasp other
than by a specialist has been devoted to this theme, which
has been studied for many years and is still growing today.
This book fills a gap in this respect, since apart from an introduction to the subject, it presents an up-to-date review
of the synthesis and properties of nucleotide analogs, taking into account the structure-function relationships. Nucleotides are described that are modified on or in the heterocycle, together with others with unusual N-glycosyl
bonds and altered sugar radicals. Moreover, the book gives
an account of the newer methods of synthesizing phosphate esters, nucleotide polyphosphates and nucleotides
with modified phosphate radicals. The final chapter deals
0 Verlog Chemie GmbH. 6940 Weinheim. 1982
with the synthesis of chemically reactive and photoreactive
derivatives, e . g . for use in affinity labeling and affinity
chromatography. Ample references at the end of each
chapter constitute an introduction to the primary literature. The many summary formula illustrations facilitate the
reading of the text. Thus, a study of this book should be
profitable both for those new to the field and for those
who have been involved in it for years. For the first of
these, it is a modern introduction, and for the latter, an upto-date summary from which they should certainly derive
stimulus for their own research.
Hubert Koster [NB 553 IE]
Ullmanns Encyklopadie der technischen Chemie. Edited by
E. Bartholomh, E. Biekerl, H . Hellmann, H . Ley (deceased), w. M . Wiegert (deceased), and E. Weise. Vol.
19: Polyacryl-Verbindungen bis Quecksilber. Verlag
Chemie, Weinheim 1980. 4th Edition, xvi, 672 pp.,
bound, DM 525.00.
This 19th volume of Ullmann's Encyclopedia"] deals
mostly with the polymers, which occupy over half of the
volume; if the biopolymers are included (proteins with 67
pp., and polysaccharides, with 31 pp.), this rises to two'*'
See Angew. Cbem. 92 (1980) 866; Angew. Cbem. Inr. Ed. Engl. 19 (1980)
0570-0833/82/0101-0084 $ 02.50/0
Angew. Cbem. in[. Ed. Engl. 21 (1982) No. I
thirds. There are two other classes of biopolymers, namely
cellulose and starches, that are not only dealt with in this
volume, but appear as cross-references to other volumes.
Further articles in this volume relate to organic intermediate products (e.g . Propanediol, 8 pp.; Propionic acid
and its derivatives, 9 pp.; Propylene, 8 pp.; Propylene oxide, I 1 pp. ; Propanol, 9 pp. ; Propanolamine, 1 1 pp.; Pyridine and its derivatives, 27 pp.), to pharmaceuticals and
their pre-products (Prostaglandins, 8 pp.; Purine and its
derivatives, 5 pp.; Pyrazolone, 8 pp.; Pyrimidine and its
derivatives, 3 pp.), to inorganic chemistry (Mercury, 29
pp.; Porcelain, 20 pp.), and to applied technologies (Pelleting compounds, 14 pp.; Powder metallurgy, 14 pp.; Pyrotechnics, 16 pp.). Of the polymers themselves, the polyolefins take up the most space with 60 pp., corresponding to
their importance, followed by the polyurethanes with 41
pp., polystyrene including its copolymers with 3 1 pp., polyacrylates and polymethacrylates with 30 pp., and finally
the polyesters with 28 pp. Under these entries for the individual classes of polymers, essentially only the manufacture and the chemical properties are dealt with, while anything to do with the application of the polymers is to be
found under other entries, mainly in Volume 15 under
Plastics or under special entries, for example Fibers, in
which, inter alia, the application of polyesters as chemical
fibers is dealt with. Special mention should also be made
of the entry on Polymerization techniques (59 pp.), which
gives a summary treatment of polymerization processes
such as solution, suspension and emulsion polymerization.
This review of an aspect of the technical production of polymers that is becoming increasingly important, fills a
long-standing gap in this area, and raises the question
whether it might not be worthwhile to expand this entry, in
due course, into a monograph. It should also be mentioned
that the entry on Proteins also gives an account of modern
methods for the biotechnological preparation of individual
proteins on the basis of unconventional carbon sources
(ethanol, alkanes). Finally, it only remains to be said that
this volume maintains the familiar high quality of UIImann's Encyclopedia, which should be available in any
chemical library on account of its information content.
Ulj-ert Onken [NB 555 IE]
Water Pollution Research and Development. Part 1-4. Executive Editor: S. H . Jenkins. Pergamon Press, New
York 1981. xii, 1388 pp., bound, $ 195.00.-lSBN 0-08026025-X
Two-phase Flows in Chemical Engineering. By D . Azbel.
Cambridge University Press, Cambridge 198 1. xx, 3 1 1
pp., bound, f 45.00.- ISBN 0-521-23772-6
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Angew. Chem. In!. Ed. Engl. 21 (1982) No. I
Die Zelle. Struktur und Funktion. Edited by H. Metzner.
Wissenschaftliche Verlagsgesellschaft, Stuttgart 1980.
3rd completely revised edition. x, 612 pp., bound, DM
96.00.- ISBN 3-8047-0607-X
Emulsion Polymers and Emulsion Polymerization. ACS
Symposium Series No. 165. Edited by D.R. Bassett and
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Insights into Chemical Engineering. (Selected Papers of P.
V. Danckwerts). By P. V. Danckwerts. Pergamon Press,
New York 1981. xviii, 307 pp., bound, $65.00.--ISBN 008-026250-3
The Peptides. Analysis, Synthesis, Biology. Vol. 4. Modern
Techniques of Conformational, Structural, and Configurational Analysis. Edited by E. Gross and J. Meienhofer.
Academic Press, New York 1981. xix, 309 pp., bound, $
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Steroid Analysis by HPLC. Recent Applications. Vol. 16.
Edited by M. f. Kautsky. Marcel Dekker, Basel 1981.
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Hummel/Scholl. Atlas der Polymer- und Kunststoffanalyse.
Band 3: Zusatzstoffe und Verarbeitungshilfsmittel. By F.
Scholl. Carl Hanser Verlag, Munchen and Verlag Chemie, Weinheim 1981. 2nd completely revised edition.
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Lehmerk Chemie-Einfiihrung in die Laboratoriumspraxis.
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Quantum Mechanics. By H. F. Harneka. Wiley-lnterscience, Chichester 1981. xii, 387 pp., bound, f 24.00.ISBN 0-47 1-09223-1
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Lasers in Chemical Analysis. Edited by G. M. Hieftje, J. C.
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The following corrections should be made to the short
communication entitled, "Di-tert-butylthia- and -selenadiphosphirane" by Marianne Baudler, Horst Suchomel, Gabriele Furstenberg, and Ulrike Schings, Angew. Chern. Int.
Ed. Engl. 20 (1981) 1044:
Vom Mythos der mathematischen Vernunft. By D. Spalt.
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On p. 1045, left-hand column:
... (tB~P)~SiPh,['l(l
: I : I), ..."
in line 13 should read:
". . . (tBuP),SiPhzf"(l : 1. I) .. ."
On the same page, same column: ". ..; but tert-butyl
groups ..." in line 49 should read: "...; but the tert-butyl
groups . ..".
Reqisiered r m t w s . irodemwhs. pic. used
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