Book Reviews REDUCTION: TECHNIQUES AND AP- PLICATIONS IN ORGANIC SYNTHESIS, Edited by Robert L. Augustine. Marcel Dekker, Inc., New York, 1968. 242 pages, indexed. Price $12.75. The proliferation of organic chem- istry reference text and methods books poses a difficult job of deciding when a book is a useful addition to a library and when the book is just another bound volume of superfluous information. Professor Augustine provides useful subject matter, brev- ity, and a relatively low price in his second volume on synthetic organic chemical procedures which make the book useful. The stated purpose is to provide concise and critical eval- uations of important synthetic re- actions for the practicing organic chemist who should be aware of all of the applications and suitability of a given reaction. While the title Reduction is too ambitious for the information contained therein, the book does go far in achieving its pur- pose. Three experts provide reviews which are comprehensive and, more importantly, are of direct utility in the laboratory. Professor Rerick's Chapter 1, "The Chemistry of the Mixed Hydrides," Dr. Smith's Chap- ter 2, "Dissolving Metal Reductions," and Professor Reusch's Chapter 3, "Deoxygenation of Carbonyl Com- 153 pounds" do creditable jobs of review- ing and interpreting the literature. The contributors include several good experimental procedures which are of immediate utility to bench chemists. One finds these procedures scattered throughout the book, but occasionally missing or insufficient in several places in Chapters 2 and 3. Sub- stantial reference sections are pro- vided at the end of each of the three chapters. Chapter 1, "The Chemistry of the Mixed Hydrides," discusses lithium aluminum hydride and sodium boro- hydride and their behavior in the presence of aluminum halides, metal salts, and alcohols to yield reducing agents of selected reactivities. Ex- perimental procedures are given for the reduction of a large number of functional groups as well as tech- niques and precautions for handling mixed hydride systems. The discussion of "Dissolving Metal Reductions" in Chapter 2 covers the recently developed metal- ammonia and metal-amine reagents as well as the older alkali metal- alcohol, metal amalgam-acid, and metal-acid systems. Experimental procedures described in this chapter are for the preparation of the reducing agent only literature references are cited for specific examples of reduc- tion. Chapter 3, "Deoxygenation of Car- bonyl Compounds," covers the Wolff-

154 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS Kishner Reduction, the Clemmensen Reduction, and desulfurization of dithioketals and dithioacetals. The chapter title is misleading since the section is devoted only to the con- version of ketone and aldehyde groups to methylene and methyl groups, respectively. Excluding this criticism, the chapter does provide a useful discussion of procedures, prob- lems, and comparisons with other, less widely used, reductive techniques. The text is quite readable, illus- trations are plentiful, printing quality is good, and there are few typographi- cal errors. This book should be pur- chased for laboratories carrying out organic syntheses.--PHILIP E. SOKOL --The Toni Company. COMPREHENSIVE ANALYTICAL CHEM- ISTRY, VOL. IIB. PHYSICAL SEPARA- TION METHODS, edited by Cecil L. Wilson and David W. Wilson. Amer- ican Elsevier Publishing Company, Inc., New York, 1968. 445 pages, $25.00. Four separation methods are in- cluded in this volume, liquid and gas chromatography, ion exchange, and distillation. In the preface the edi- tors apologize that circumstances prevented inclusion of a chapter de- scribing paper and thin-layer chro- matography. This is regrettable, but it is by no means the sole fault of this book ! The purpose of this volume, as stated in the preface by the editors, is to provide a self-sufficient, detailed compendium of methods for prac- ticing analytical chemists. I would expect from such statements, and from the title, to find a substantial number of methods, each supported by a discourse of theoretical back- ground and in sufficient detail to apply them directly in the laboratory. Clearly, this is not the case! In- stead, I found but 10 specific methods and all in the one chapter dealing with ion exchangers. The preface also states that this volume provides full references to the pertinent literature whenever details of the methods cannot be given. Once again the book fails the refer- ences are inadequate. Of 225 refer- ences to the ion exchange literature, I found only 21 from the years 1957- 1965 inclusive and none from a later date. Even more disappointing were the references to the gas chromatog- raphy literature. With the bur- geoning literature in this field since 1963, I expected more than 62 refer- ences covering the period out of the total list of 446. (There are no ref- erences to work later than 1966.) A specific example of the volume's in- adequacy as a reference text is in the gc applications section dealing with amino acids. There are only six references in this section, all to work published in 1962 and earlier. Com- pletely omitted are references to the more recent and useful work of such well-known investigators as Blau and Darbre, Gehrke and co-workers, and Shlyapnikov and co-workers. I have a number of other books in my library which serve the same pur- pose as this book--only better. I don't think I'll add this one to the collection.--R. F. SCHUBERT--The Toni Company.