Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, NJ 08854 (USA).
Angew Chem Int Ed Engl. 2013 Oct 18;52(43):11222-51. doi: 10.1002/anie.201209833. Epub 2013 Sep 23.
It has been 60 years since Eschenmoser and Frey disclosed the archetypal CC fragmentation reaction. New fragmentations and several variants of the original quickly followed. Many of these variations, which include the Beckmann, Grob, Wharton, Marshall, and Eschenmoser-Tanabe fragmentations, have been reviewed over the intervening years. A close examination of the origins of fragmentation has not been described. Recently, useful new methods have flourished, particularly fragmentations that give alkynes and allenes, and such reactions have been applied to a range of complex motifs and natural products. This Review traces the origins of fragmentation reactions and provides a summary of the methods, applications, and new insights of heterolytic CC fragmentation reactions advanced over the last 20 years.
自 Eschenmoser 和 Frey 揭示典型的 CC 断裂反应以来已经过去了 60 年。随后很快出现了新的断裂和原始反应的几种变体。这些变体中的许多，包括 Beckmann、Grob、Wharton、Marshall 和 Eschenmoser-Tanabe 断裂，在过去的几年中都得到了综述。对断裂的起源并没有进行详细的描述。最近，新的有用方法蓬勃发展，特别是生成炔烃和丙二烯的断裂，并且这些反应已经应用于一系列复杂的模体和天然产物。这篇综述追溯了断裂反应的起源，并提供了过去 20 年来杂原子诱导的 CC 断裂反应方法、应用和新见解的总结。
