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The Grob/Eschenmoser fragmentation of cycloalkanones bearing β-electron withdrawing groups: a general strategy to acyclic synthetic intermediates.

Research paper by Judith J Hierold, Tina T Hsia, David W DW Lupton

Indexed on: 26 Nov '10Published on: 26 Nov '10Published in: Organic & Biomolecular Chemistry



Abstract

Introduction of a β-electron withdrawing group to cycloalkanones allows facile C-C bond fragmentation. The reaction has been demonstrated with a large range of ring sizes, bearing various leaving and electron withdrawing groups, and using a variety of nitrogen and oxygen containing nucleophiles (>30 examples). The application of fragmentation products to the preparation of substituted γ-lactones has been demonstrated. Mechanistic studies are reported which are suggestive of a Grob/Eschenmoser type reaction.