1
dust is still an extremely useful method in structural investi- gations when known rearrangements are borne in mind. B. C. L. Weedon reviews the applications of alkali fusion and the re- actions that occur thereby. Relatively unknown reactions, such as the alkyl transfer to ketones, special dehydrogenations of alkoxides, and the demethylation of methoxylated phenols are mentioned. J. K. N. Jonesand M. 3. Perry discuss methods for degrading polysaccharides and methylated polysaccha- rides. K. W. Bentley describes the application of conventional methods of cleaving C-0 and C-N bonds mainly in the alkaloid series. The reviewer welcomes the inclusion of the little known cleavage of N-CH3 bonds with azodicarboxylic esters discovered by 0. Diels and of the @elimination with LiAIH4. E. Y. Spencer gives a thirty page review of methods for the hydrolytic degradation and elucidation of the struc- tures of polypeptides and proteins, including a discourse on oxidative procedures. K. T. Ports illustrates the application of known methods of cleaving C=C bonds with examples from the chemistry of natural products. The interesting cleavages that occur with alkaline H202 are relatively unknown. A second article by K. W. Bentley on C=C fission reports mainly on common methods; the examples given of abnormal cleavage with ozone are highly instructive. The chapter by N. Polgar on methods for shortening side chains and long- chained compounds is also very useful as it describes rela- tively unfamiliar reactions. Here brevity does not permit a closer appraisal of the excel- lent article (150 pages) by 3. Belleau oil the allocation of steric configurations to natural products using chemical meth- ods. This article also describes the latest data on reaction mechanisms and can be recommended as the basis of lectures on stereochemistry. In the final article, P. de Mayo writes a most intriguing review of rearrangement reactions that occur with natural products. Only one (see p. 1095) of the few print- ing and formulae errors is not immediately recognizable: here an attacking proton is drawn directly above an angular methyl group. This volume deserves a hearty recommenda- H. Plieninger [NB 2561114 IE] tion. Infrared Band Handbook. Edited by H. A. Szymnnski. Plenum Press, New York 1963. 1st Edit., xii + 484 pp., linen $7.50. This book is a catalogue of over 8500 infrared bands in the region between 3610 and 617 cm-1, measured on over a thousand substances. In the main part of the volume, the bands are arranged in order of decreasing wave-number. The information for each band comprises, as far as possible, sub- stance, nature of sample measured, resolution of instrument, type of vibration, band intensity, and reference. The book con- tains also a substance index and correlation tables for methyl deformation vibrations and C-N valence vibrations, since these vibrations are not included in the main section. The literature references have been restricted to 25 sources cover- ing the period up to 1961. The principal source evaluated is the American Petroleum Research Institute, Project 44 catalogue. Annual supplements costing $7.50 are planned to cover the region down to 250 cm-1. The book is a valuable aid for the identification of unknown substances and for the solution of problems of band assignment. [NB 26111 19 IE] E. Lipperf Oxydation des MBtaux (Oxidation of Metals). Vol. I: Pro- cessus Fondamentaux (Fundamental Processes). Edited by J. BPnard. Gauthiers-Villars et Cie., Paris 1962. 1st Edit., 465 pp., numerous illustrations, linen, NF 55.- (about $11.50). theories and for development of more refined concepts. In this first of two volumes on the “Oxidation of Metals” J. Benard and a number of collaborators have attempted to give a de- tailed account of the fundamental principles involved, with- out omitting any relevant material. A brief glance at the coii- tents of the various chapters may serve to illustrate this point. Chapters 1-5: Metal surfaces, adsorption equilibria, the ki- netics of adsorption and chemisorption, the structure of chemisorption layers and their influence on the properties of the underlaying metal (J. BPnard). Chapters 6-8: Nucleation processes, the growth of thin layers and their orientation (J. Benard, J. Bardollc, and F. Bouillon). Chapters 9-1 I : Thicker layers, methods of investigation and results, diffusion theory of layer formation (G. Valensi). Chapters 12-15: Thermo- dynamics and kinetics of the oxidation of alloys, internal oxi- dation (J. Morenu and J. BPnnrd). Chapter 16: Real structure of oxides, mechanical properties, dislocations, etc. (M. Cagnet). Tables of crystallographic, thermal, and mechanical properties of metal oxides are also given. The individual contributors do not always adopt the same approach to their readers. Thus, for example, a detailed deri- vation of the law of diffusion is given (p. 228), but sometimes simply the results of rather complex theorems are given, e.g. for internal oxidation. Nevertheless, the book offers an ex- cellent provocative and modern survey of the subject, and topics that are all too frequently neglected (e.g. the morpho- logical and mechanical properties of metal/metal oxide sys- tems) are considered, as is to be expected from this editor and his coworkers. English, French, and German literature has been covered thoroughly and uniformly until 1960 (1052 W. Jaenicke [NB 268/125 IE] references). Steroid Reactions: An Outline for Organic Chemists. Edited by C. Djerassi. Holden-Day, Inc., San Francisco 1963. 1st Edit., vi + 657 pp., linen $9.75. C. Djerassi maintains that the increasing profusion of publi- cations connected with the field of steroids has led many chem- ists who are not familiar with this subject to abandon the practice of reading articles devoted to it. This is regrettable insofar as there is hardly a chemical reaction that has not been applied to steroids. Furthermore the reactions applied have frequently led to particularly lucid results because of the relatively precise knowledge of the structures, conformations, and reactivities of steorid derivatives. In order to break the soil of this fallow field and make it available even to non- steroid chemists, 16 post-graduate students at Stanford Uni- versity undertook to arrange 14 special aspects of the subject into order in the form of formulae schemes under Djerassi’s guidance; the appropriate reaction conditions, yields, and literature references are given for each reaction. The data include the protection of carbonyl and hydroxyl groups, selective oxidation of polyhydroxysteroids, the introduction of fluorine into the steroid system, the production and de- hydrohalogenation of a-bromo, or-chloro, and or-iodo keto- steroids, erc. Apart from short introductions before the chap- ters, written text has been completely replaced by formulae and reaction schemes. Thus it is simple for the user of the book to survey the general picture, and this helps him to find any desired reaction rapidly. Since the work done by the students has been checked and supplemented by experienced steroid chemists in large American firms, the result is an ex- cellent review volume which undoubtedly fully achieves its aim of providing a rapid guide to the entire subject and which will therefore soon acquire many friends. The book fills an obvious gap, even though it is not completely free from errors; one must expect this when one considers the abundance of material discussed. However, the reviewer doubts whether it will influence many non-steroid chemists into investigating the ever increasing amount of steroid literature. In any case, it will certainly be often consulted by the specialist in this field. R. Tschesclre [NB 285/143 IE] Over the past few years, experiments on the oxidation of me- tals have been carried out increasingly under carefully con- trolled conditions and with highly purified starting materials. The time therefore seemed ripe for reassessment of existing Angew. Chem. internat. Edit. 1 Vol. 4 (1965) 1 No. 2 179

Book Review: Infrared Band Handbook. Edited by H. A. Szykmanski

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dust is still an extremely useful method in structural investi- gations when known rearrangements are borne in mind. B. C. L. Weedon reviews the applications of alkali fusion and the re- actions that occur thereby. Relatively unknown reactions, such as the alkyl transfer to ketones, special dehydrogenations of alkoxides, and the demethylation of methoxylated phenols are mentioned. J. K. N. Jonesand M. 3. Perry discuss methods for degrading polysaccharides and methylated polysaccha- rides. K . W. Bentley describes the application of conventional methods of cleaving C - 0 and C-N bonds mainly in the alkaloid series. The reviewer welcomes the inclusion of the little known cleavage of N-CH3 bonds with azodicarboxylic esters discovered by 0. Diels and of the @elimination with LiAIH4. E. Y . Spencer gives a thirty page review of methods for the hydrolytic degradation and elucidation of the struc- tures of polypeptides and proteins, including a discourse on oxidative procedures. K . T. Ports illustrates the application of known methods of cleaving C=C bonds with examples from the chemistry of natural products. The interesting cleavages that occur with alkaline H202 are relatively unknown. A second article by K . W. Bentley on C=C fission reports mainly on common methods; the examples given of abnormal cleavage with ozone are highly instructive. The chapter by N. Polgar on methods for shortening side chains and long- chained compounds is also very useful as it describes rela- tively unfamiliar reactions.

Here brevity does not permit a closer appraisal of the excel- lent article (150 pages) by 3. Belleau oil the allocation of steric configurations to natural products using chemical meth- ods. This article also describes the latest data on reaction mechanisms and can be recommended as the basis of lectures on stereochemistry. In the final article, P. de Mayo writes a most intriguing review of rearrangement reactions that occur with natural products. Only one (see p. 1095) of the few print- ing and formulae errors is not immediately recognizable: here an attacking proton is drawn directly above an angular methyl group. This volume deserves a hearty recommenda-

H. Plieninger [NB 2561114 IE] tion.

Infrared Band Handbook. Edited by H. A . Szymnnski. Plenum Press, New York 1963. 1st Edit., xii + 484 pp., linen $7.50.

This book is a catalogue of over 8500 infrared bands in the region between 3610 and 617 cm-1, measured on over a thousand substances. In the main part of the volume, the bands are arranged in order of decreasing wave-number. The information for each band comprises, as far as possible, sub- stance, nature of sample measured, resolution of instrument, type of vibration, band intensity, and reference. The book con- tains also a substance index and correlation tables for methyl deformation vibrations and C-N valence vibrations, since these vibrations are not included in the main section. The literature references have been restricted to 25 sources cover- ing the period up to 1961. The principal source evaluated is the American Petroleum Research Institute, Project 44 catalogue. Annual supplements costing $7.50 are planned to cover the region down to 250 cm-1. The book is a valuable aid for the identification of unknown substances and for the solution of problems of band assignment.

[NB 26111 19 IE] E. Lipperf

Oxydation des MBtaux (Oxidation of Metals). Vol. I : Pro- cessus Fondamentaux (Fundamental Processes). Edited by J. BPnard. Gauthiers-Villars et Cie., Paris 1962. 1st Edit., 465 pp., numerous illustrations, linen, N F 55.- (about $11.50).

theories and for development of more refined concepts. In this first of two volumes on the “Oxidation of Metals” J . Benard and a number of collaborators have attempted to give a de- tailed account of the fundamental principles involved, with- out omitting any relevant material. A brief glance at the coii- tents of the various chapters may serve to illustrate this point. Chapters 1-5: Metal surfaces, adsorption equilibria, the ki- netics of adsorption and chemisorption, the structure of chemisorption layers and their influence on the properties of the underlaying metal (J . BPnard). Chapters 6-8: Nucleation processes, the growth of thin layers and their orientation ( J . Benard, J . Bardollc, and F. Bouillon). Chapters 9-1 I : Thicker layers, methods of investigation and results, diffusion theory of layer formation ( G . Valensi). Chapters 12-15: Thermo- dynamics and kinetics of the oxidation of alloys, internal oxi- dation (J. Morenu and J. BPnnrd). Chapter 16: Real structure of oxides, mechanical properties, dislocations, etc. ( M . Cagnet). Tables of crystallographic, thermal, and mechanical properties of metal oxides are also given. The individual contributors do not always adopt the same approach to their readers. Thus, for example, a detailed deri- vation of the law of diffusion is given (p. 228), but sometimes simply the results of rather complex theorems are given, e . g . for internal oxidation. Nevertheless, the book offers an ex- cellent provocative and modern survey of the subject, and topics that are all too frequently neglected (e.g. the morpho- logical and mechanical properties of metal/metal oxide sys- tems) are considered, as is to be expected from this editor and his coworkers. English, French, and German literature has been covered thoroughly and uniformly until 1960 (1052

W. Jaenicke [NB 268/125 IE] references).

Steroid Reactions: An Outline for Organic Chemists. Edited by C. Djerassi. Holden-Day, Inc., San Francisco 1963. 1st Edit., vi + 657 pp., linen $9.75.

C. Djerassi maintains that the increasing profusion of publi- cations connected with the field of steroids has led many chem- ists who are not familiar with this subject to abandon the practice of reading articles devoted to it. This is regrettable insofar as there is hardly a chemical reaction that has not been applied to steroids. Furthermore the reactions applied have frequently led to particularly lucid results because of the relatively precise knowledge of the structures, conformations, and reactivities of steorid derivatives. In order to break the soil of this fallow field and make it available even to non- steroid chemists, 16 post-graduate students at Stanford Uni- versity undertook to arrange 14 special aspects of the subject in to order in the form of formulae schemes under Djerassi’s guidance; the appropriate reaction conditions, yields, and literature references are given for each reaction. The data include the protection of carbonyl and hydroxyl groups, selective oxidation of polyhydroxysteroids, the introduction of fluorine into the steroid system, the production and de- hydrohalogenation of a-bromo, or-chloro, and or-iodo keto- steroids, erc. Apart from short introductions before the chap- ters, written text has been completely replaced by formulae and reaction schemes. Thus it is simple for the user of the book to survey the general picture, and this helps him to find any desired reaction rapidly. Since the work done by the students has been checked and supplemented by experienced steroid chemists in large American firms, the result is an ex- cellent review volume which undoubtedly fully achieves its aim of providing a rapid guide to the entire subject and which will therefore soon acquire many friends. The book fills an obvious gap, even though it is not completely free from errors; one must expect this when one considers the abundance of material discussed. However, the reviewer doubts whether it will influence many non-steroid chemists into investigating the ever increasing amount of steroid literature. In any case, it will certainly be often consulted by the specialist in this field.

R. Tschesclre [NB 285/143 IE]

Over the past few years, experiments on the oxidation of me- tals have been carried out increasingly under carefully con- trolled conditions and with highly purified starting materials. The time therefore seemed ripe for reassessment of existing

Angew. Chem. internat. Edit. 1 Vol. 4 (1965) 1 No. 2 179