Six-Membered Transition States in Organic Synthesis

Fifty years ago, Zimmerman and Traxler put forth an audacious suggestion that in a reaction they were studying six of the atoms were oriented in a ring as the two components approached each other. This was at a time when no one considered the detailed orientation of molecules during reactions. This Zimmerman-Traxler hypothesis is now known to be not only correct for their reaction, but in fact true in many other chemical processes. As such, the idea is one of the fundamental organizing principles of organic chemistry. Yang (Montana State Univ.) has provided a useful collection of all reactions currently understood to proceed in such fashion. These reactions are contained in 4 chapters: "[3,3] - Sigmatrophic Rearrangements," "Aldol Reactions," "Metal Allylation Reactions," and "Stereoselective Reductions." This small book should be useful for both synthetic chemists and those studying mechanisms, particularly stereochemistry, of organic reactions. Summing Up: Recommended. Upper-division undergraduate through professional collections. -- A. Fry, Wesleyan University (CHOICE, March 2009)

It is an interesting, well-written, and carefully researched book, full of useful details for practioners and students of organic chemistry. (Journal of the American Chemical Association, July 2, 2008)