Chemical Education Today edited by
Book & Media Reviews
Jeffrey Kovac University of Tennessee Knoxville, TN 37996-1600
Named Organic Reactions, Second Edition by Thomas Laue and Andreas Plagens John Wiley & Sons: Chichester, England, New York, 2005. 320 pp. ISBN 047001041X (paper). $55. ISBN 0470010401 (cloth). $125
Name Reactions and Reagents in Organic Synthesis, Second Edition by Bradford P. Mundy, Michael G. Ellerd, and Frank G. Favaloro John Wiley & Sons: Hoboken, NJ, 2005. 882 pp. ISBN 0471228540 (cloth). $89.95. [E-book also available as a digital download using Adobe Reader 6.x or 7.0: Wiley-Interscience: New York, 2005. Mac OS 10.2.8 and above, Windows, Palm OS devices (but not Pocket PC or Symbian devices); Adobe Reader required. ISBN 0471739863. $89.95]
Strategic Applications of Named Reactions in Organic Synthesis: Background and Detailed Mechanisms László Kürti and Barbara Czakó Elsevier Academic Press: Burlington, MA, 2005. 864 pp. ISBN 0124297854 (paper). $94.95. ISBN 01233694833 (hardcover with CD-ROM). $169.95 ISBN 0123694825 (PDF Edition); $94.95 reviewed by R. W. Holman
edition bearing the current name was published in English in 1998. The new second edition is pedagogically superior to the first edition, having been completely revised in both style and content. It is a collection of 134 of the most common named organic reactions, with “common” being defined as those reactions most likely addressed in the combination of a typical sophomore organic chemistry sequence plus an advanced undergraduate–beginning graduate organic reactions and synthesis course. The discussion of each reaction begins with a one-sentence description and a scheme, followed by a detailed introductory treatment including a detailed step-by-step mechanism. Examples of the applications of the particular reaction are given along with a reference to the very first publication of the reaction, to show the origin of its name and how it was explored or developed. Additionally, review articles are cited, together with recent articles. This volume reads like a textbook insofar as it contains detailed paragraphs accompanying the descriptions of the reaction in view. Laue and Plagen’s Named Organic Reactions is an indispensable resource for an advanced undergraduate or beginning graduate student taking an organic reaction course; it can, in fact, work well as a textbook (or text supplement) for such a course (save for the fact that there are no problems or exercises). Further, research students could gain much from this book as the essential nature of each of the reactions addressed in the book is presented in sufficient detail that the reaction can be well understood without the need to consult any other resource (and yet one can go to ample additional resources if desired based upon the rather complete literature citations provided). Here depth of coverage and sufficient detail to be a first-exposure single-source teaching tool is emphasized at the expense of breadth of coverage.
Name Reactions and Reagents in Organic Synthesis In the world of bikes, there is a vast array of choices that differ markedly, yet generally bear the same name—cross country, downhill, freestyle, hardtail, and dual suspension bikes are all referred to simply as mountain bikes. The casual observer would be at a loss to decide which bike to purchase. All the choices, generally speaking, get the job done, but the best choice for you depends on the application. How one plans to use the bike is the best guide for which bike to chose. Similarly, there is an array of newly released books with some form of “Named Organic Reactions” in the title; three are reviewed here. Of these new books, which one should you choose? In this composite review, the goal is to illustrate the differences in the scope and scale of these similarly titled books so the reader may determine the book that best fits his or her needs.
Named Organic Reactions The second edition of Named Organic Reactions has its origin in 1995 in Laue and Plagen’s German work, Namenund Schlagwort-Reaktionen der Organischen Chemie. The first
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In contrast, the second edition of Name Reactions and Reagents in Organic Synthesis is a much more exhaustive collection, addressing more than 500 reactions (and rearrangements). The breadth of coverage extends well beyond the confines of a typical undergraduate–beginning graduate organic chemistry course, although the detail presented for each reaction is minimal. The intent is not so much to be a singlesource teaching tool or text or text supplement covering that subset of reactions germane to university classes in organic chemistry as it is to be a much more comprehensive reference work that is most suitable for synthetic chemists. Reactions are listed alphabetically, each listing providing either an accepted or a proposed mechanism (often with minimal detail), along with secondary information, and two to four examples with citations. In addition to literature citations, when applicable the reactions are cross-referenced to Laue and Plagen’s, Named Organic Reactions (2nd edition) or Jerry March’s Advanced Organic Chemistry (5th edition); WileyInterscience publishes all three books. Name Reactions and Reagents in Organic Synthesis also contains an extremely use-
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Chemical Education Today
Book & Media Reviews ful (and unique) second section that lists alphabetically more than 200 named reagents and reagent acronyms; each entry lists the reagent’s structure, its major uses and preparation, commercial availability, necessary precautions, secondary information, and two or three referenced applications. Unlike Laue and Plagens, this book does not include commentary and is not structured to be a direct teaching tool, rather it is a launching point to a vast array of named chemical reactions.
Strategic Applications of Named Reactions in Organic Synthesis Different still is the work of Kürti and Czakó. The authors use a two-page format that uses four-color graphics to address 250 reactions selected for inclusion based upon their applicability to modern natural products synthesis. Each named reaction is concisely introduced, mechanistically explained, and then set in context with example applications involving the production of natural products. Almost 10,000 references are indexed at the end of the book, subdivided into three groups for each reaction: seminal publications, reviews, and modifications/improvements. It is not uncommon to have as many as 70 references for a given reaction. Also included is a comprehensive list of abbreviations used in the text or drawings along with the structure of any protecting groups or reagents utilized. Also in an appendix, the named organic reactions are grouped on the basis of their use in contemporary synthesis, being organized by affected functional
Authors, Edition
Number of Reactions
Basis of Coverage
Laue and Plagens; 2nd edition
134+
Sophomore level– beginning graduate course common reactions
Mundy, Ellerd, and Favaloro; 2nd edition
500+
Near total coverage of all named reactions currently utilized
Kürti and Czakó; 1st edition
250+
Synthetic utility in natural product chemistry
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group, newly formed functional group, or reaction category. Thus the reader can readily ascertain which named organic reactions effect the functional group transformation that is of interest. This book is outstanding in every way, being polished in presentation, sufficiently detailed in explaining the reactions, and possessing almost encyclopedic indexing and referencing. The similarities and differences in the three books are summarized in the table. So which bike do you ride? All three books, similarly titled and all excellent contributions to the field, are nevertheless quite different from one another. I hope this compare and contrast overview will help you determine which works best for you. As for me, I own five different mountain bikes and all three books—what more can one ask for than a full garage and a full book shelf! R. W. Holman is in the Department of Chemistry, Idaho State University, Pocatello, ID 83209;
[email protected] Editor’s Note: JCE ChemInfo Organic (http://www.jce.divched.org/ JCEDLib/ChemInfo/Organic) lists 95 of the most important named reactions, each linked to a Web page that gives primary references and equations. It also provides a list of 160 common named reagents as well as concise descriptions of a number of named effects.
Written Analysis
Number of References
Unique Features
Extensive
3–15 per reaction
Reads like a text and provides detailed treatments
None
3–10 per reaction and references to Laue and Plagens
General reference, and addresses named reagents
Modest
20–70 per reaction
General reference and extensive indexing and referencing
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