The Chemical Educator, Vol. 5, No. 2, S1430-4171(00)02374-7, 10.1007/s00897990374a, 2000 Springer-Verlag NewYork, Inc.

Named Organic Reactions. By Thomas Laue and Andreas Plagens, John Wiley & Sons: Chichester, England, New York, 1998. Structural formulas, reaction schemes. x + 288 pp. 15.6 23.5 cm. $69.95, hardcover. ISBN 0-471-97142-1.

Reviewed by: George B. Kauffman, California State University, Fresno, george_kauffman@csufresno.edu

Originally published in German as Namen- und Schlagwort-Reaktionen der Organischen Chemie (B. G. Teubner: Stuttgart, Leipzig, Germany, 1995), this handy source book by Thomas Laue and Andreas Plagens of the Technische Universität Braunschweig has now been felicitously translated into English by Claus Vogel of the Universität Magdeburg. According to the authors, "Name reactions are still an important element of organic chemistry .... used as short expressions in order to ease spoken as well as written communication .... [They] are a perfect aid for learning the principles of organic chemistry."

Their book is not intended to replace an organic chemistry textbook but is "a reference work on name reactions, that is also suitable for easy reading and learning, as well as for review for an exam in organic chemistry." This compact collection contains accounts of 112 (the authors claim that it contains 134) significant named reactions from classical and modern organic chemistry, alphabetically arranged from the acyloin ester condensation to the Wurtz reaction and ranging in length from one page (Delépine reaction) to more than six or seven pages (Diels–Alder and Grignard reactions, respectively). Ninety-eight of the reactions bear the names of their discoverers, while the remaining 14 are named for the type of reaction such as diazo coupling, glycol cleavage, haloform, hydroboration, malonic ester synthesis, ozonolysis, and vinylcyclopropane rearrangement. The selection has been made based on their importance for modern preparative organic chemistry and for today's organic chemistry courses.

Each section begins with the name of the reaction, followed by a subtitle giving a one-sentence description, a formula scheme depicting the overall reaction, and an initial paragraph with an introductory description. The major portion of each section presents clearly outlined reaction mechanisms, side-reactions, and variants, and modified procedures with respect to product distribution and yields. Recent and older examples of the application of the particular reaction or method are given along with references to the original literature; these examples are not intended to deal with every aspect but are chosen from a didactic viewpoint for advanced students. In addition to the reference to the very first publication to show the origin of the reaction's name and how it was explored or developed, review articles are cited, together with recent articles. A 4-page (2 columns per page) index facilitates location of material.

Thumbnail sketches of the discoverers would have added another dimension for those interested in the history of organic chemistry, but sketches would have added to the length and cost of the volume. For example, British historian of chemistry Peter J. T. Morris is currently writing a commissioned article on relatively unknown discoverers of name reactions and is particularly interested in the few women chemists in this category. Thumbnail sketches would have disclosed that the discoverers of the Hunsdiecker reaction (which is included) and the Piloty–Robinson reaction (not included) were wives of the chemists involved. Most of the principal name reactions of organic chemistry are represented in Laue and Plagens' collection, an exception being the Ullmann reaction (coupling of two aromatic nuclei on heating aryl iodides with activated copper), of which I am reminded only by my recent review of Ullmann's Encyclopedia of Industrial Chemistry in The Chemical Educator (1999, 5(1) 49-52).

As a result of reviewing Named Organic Reactions, the next time I stub my toe during nocturnal wanderings in the dark and exclaim "Hell–Volhard–Zelinskii," I will do so with the additional insight that "an a-hydrogen of a carboxylic acid can be replaced by bromine or chlorine to give an a-bromo- or a-chlorocarboxylic acid, respectively." And for lesser catastrophes, where the Heck reaction will suffice for my expletive, I'll recall "the palladium-catalyzed carbon–carbon coupling of an alkyl, aryl, or vinyl group to an alkene."