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Synthesis 1991; 1991(5): 357-361
DOI: 10.1055/s-1991-26465
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Oxidative Rearrangement of Phosphorus Containing Tertiary Allylic Alcohols: Synthesis of (3-Oxo-1-cycloalkenyl)phosphonates, -methylphosphonates, -methyldiphenylphosphine Oxides and Their Epoxy Derivatives

Elisabeth Öhler* , Erich Zbiral
  • *Institut für Organische Chemie der Universität Wien, Währingerstraße 38, A-1090 Wien, Austria
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Publication Date:
29 April 2002 (online)

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Regioselective 1,2-addition of dimethyl phosphite, diethyl (lithiomethyl)phosphonate, or (lithiomethyl)diphenylphosphine oxide to 2-cyclopenten-1-one (1a) or 2-cyclohexen-1-one (1b) affords the corresponding phosphorus containing, tertiary allylic alcohols 2-4. These, upon oxidation with chromium trioxide reagents are rearranged to the new dialkyl (3-oxo-1-cycloalkenyl)phosphonates, -methylphosphonates or [(3-oxo-1-cycloalkenyl) methyl]diphenylphosphine oxides 5-7, which are easily transformed to the corresponding epoxy derivatives 8-10.