C-C fragmentation: Origins and recent applications

Michael A. Drahl, Madhuri Manpadi, Lawrence J. Williams

Research output: Contribution to journalArticlepeer-review

90 Scopus citations


It has been 60 years since Eschenmoser and Frey disclosed the archetypal C-C 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 C-C fragmentation reactions advanced over the last 20 years.

Original languageEnglish (US)
Pages (from-to)11222-11251
Number of pages30
JournalAngewandte Chemie - International Edition
Issue number43
StatePublished - Oct 18 2013

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)


  • alkenes
  • alkynes
  • allenes
  • natural products
  • synthetic methods


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