Diazo compounds, ranging from simple diazoalkanes to highly substituted diazocarbonyl compounds, play an important role in modern organic synthesis. With the development of new catalysts for their decomposition, diazo "reagents", particularly the diazocarbonyl species, can be used in chemoselectively, regioselectively, and stereoselectively controlled ways to generate carbon-carbon and carbon-hetero bonds. Doyle, McKervey, and Ye have written a comprehensive and well-organized review of this aspect of synthetic chemistry.

The book emphasizes the chemistry of diazocarbonyl compounds rather than the parent diazoalkanes. Chapter 1, after a brief description of the early history of the compounds, is concerned with methods for their preparation. These include acylation of diazoalkanes (e.g., the classical reaction of diazomethane with an acid chloride), diazo transfer processes, and other methods in which a variety of functional groups such as oximes or tosylhydrazones are converted into alpha-diazo carbonyls.

Chapter 2 is a review of the chemistry of catalysts used for diazo decomposition, including discussion of catalytic cycles. Succeeding chapters discuss C-H bond insertion reactions, intermolecular and intramolecular cyclopropanation, and aromatic reactivity toward diazocarbonyls in both cycloaddition and substitution processes. Discussions of the preparation of ylides, hetero atom X-H insertion, the Wolff rearrangement, and the synthetically powerful methods resulting from the reactivity of diazocarbonyls toward aldehydes, ketones, and their unsaturated analogues are given in later chapters. The last chapter covers the always-necessary review of "miscellaneous" reactions that do not fit other classifications of reactivity.

The authors have attempted in admirable fashion to cover not only examples of what has been done in diazocarbonyl chemistry, but also how to do it. Each chapter includes several specific experimental procedures excerpted from a wide variety of original sources. Thus the volume can be used as a guide to the literature and as a collection of empirical "templates" for the laboratory. With this emphasis on the practical as well as the bibliographical aspects of the subject comes a necessary focus on the safety issues associated with diazo compounds.

The literature coverage is excellent, each chapter being followed by extensive references relating to that specific topic. These references are largely from recent literature (1970-1995). Significant reviews are cited for older work. Another admirable feature of the book is the authors' focus on the use of diazocarbonyls in natural product synthesis. Although they do not include total syntheses they frequently and usefully describe or outline the pathway to a target molecule following the key diazocarbonyl insertion, cycloaddition, or cyclization step used for a variety of biologically interesting compounds.

The organization of the chapters is clear and logical. For example, in Chapter 3, "Intramolecular Cyclopropanation and Related Addition Reactions", the authors first discuss cyclopropanation with diazoketones and then with diazoesters and amides. They then can review the questions of selectivityregioselectivity and chemoselectivity, enantioselectivity and diastereocontrol. Macrocyclic cyclopropanation and cyclopropenation reactions follow.

On reading the introduction in Chapter 1, the reader of this book may at first be alarmed at the authors' style. The first sentence is Faulknerian, ten lines long with a variety of parenthetical clauses and asides. In happy contrast to the beginning, however, is the clear, direct, and engaging prose style that characterizes the rest of the volume. The book is a pleasure to read and will be readily accessible to students as well as to more sophisticated workers in the field.

In conclusion, the authors, Doyle, McKervey, and Ye, have produced an outstanding review of modern diazocarbonyl chemistry, have shown how that chemistry can be used in synthesis, and have provided, through literature citations and specific experimental procedures, a ready access to the interesting chemistry and the usefulness of alpha-diazocarbonyl compounds.