Chemical Education Today
Book & Media Reviews
edited by
Edward J. Walsh Allegheny College Meadville, PA 16335
Transition Metals in the Synthesis of Complex Organic Molecules, 2nd Edition by L. S. Hegedus University Science Books: Sausalito, CA, 1999. 352 pp. ISBN 1-891389-04-1. $48.00. reviewed by Peter Wipf
This book is an update of the popular 1994 edition of Hegedus’ organometallic digest for synthetic organic chemists. Literature is now covered through mid-1999. Considering the rapid expansion of the use of organometallic reagents in synthesis during the past five years, such a revision is very timely. It is difficult to find another text that has the superb qualities of the Hegedus volume—in particular, its appeal to practitioners of the art of organic synthesis in industry and academe, and its breadth, which makes it particularly suitable as a textbook for an advanced undergraduate course in organometallic chemistry or an introductory level graduate course in synthetic applications of transition metal chemistry. Experts who are looking for detailed discussions of organometallic reaction mechanisms or subtleties of transition metal coordination chemistry will be disappointed, however, since the book is mainly written as an overview of the basic reaction principles. Several hundred new references have been added in the second edition, and several chapters have been revised. While the discussions of formalisms and mechanisms and much of hydrogenation (Chapters 1–3) remained unchanged, Chapter 4, on the chemistry of σ-alkyl metal complexes, has been expanded. This chapter comprises some of the favorites of current synthetic organic methodology such as the Heck, Stille, and Suzuki couplings. Surprisingly, Pd- and Ni-mediated aniline and aryl ether formations, which have become extremely popular in industrial research labs are still conspicuously absent. Only small modifications from the first edition can be
noted in Chapters 5 and 8, which treat metal carbonyl and alkyne (e.g., Pauson–Khand) chemistry, respectively. Chapter 6 deals with metal carbene chemistry and is considerably expanded in the sections on group 6 carbenes, Rh(II)-catalyzed decomposition of diazo compounds, and ring closing metathesis. Although the reference section on the last topic has been updated, the space given to the discussion of RCM strategies in the text does not yet reflect the major significance of this new organometallic process or the wide range of new catalysts that have been discovered recently. In Chapter 7, a new section on metal-catalyzed cycloadditions has been added. The p-allyl chemistry of palladium now includes a discussion of asymmetric induction, and new chemistry of metal arene complexes has been added to Chapter 10. Unfortunately, with the introduction of new, more complex examples in this edition, the number of typographical errors and omissions in the schemes has ballooned. While the lack of information on yields, selectivities, solvents, temperature, or reaction times in the schemes will force some readers to go to the primary literature to get the complete picture, students might be more negatively affected by the relatively large number of structural typos in the schemes. These range from the cosmetic (page 66, Figure 4.3—a renegade wedge; inappropriate substituents in eq 4.57) to lack of stereochemical markers (eq 4.51 on page 81) to wrong products (eqs 4.59, 4.98, 4.100, 4.108) and ghost referrals (eq 4.37 on line 8, page 76), to name just a few. One can only hope that the publisher is already working on a revision in which these distracting errors have been weeded out. In summary, the second edition of this unique text by Hegedus is significantly updated over the first edition and continues to provide a very valuable and reasonably priced resource on the practical uses of transition metals in synthetic organic chemistry. Peter Wipf is in the Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260.
JChemEd.chem.wisc.edu • Vol. 77 No. 4 April 2000 • Journal of Chemical Education
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