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C[BOND]C Fragmentation: Origins and Recent Applications

Authors

  • Michael A. Drahl,

    1. Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, NJ 08854 (USA)
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  • Prof. Madhuri Manpadi,

    1. Walter H. Hoffman Department of Chemistry, Drury University, 900 North Benton Avenue, Springfield, MO 65802 (USA)
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  • Prof. Lawrence J. Williams

    Corresponding author
    1. Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, NJ 08854 (USA)
    • Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, NJ 08854 (USA)

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Abstract

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

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