Oxidation of fluoroalkyl-substituted allylic alcohols: A synthesis of fluorinated α,β-epoxyketones

Article abstract of DOI:10.1007/BF01435797

Fluoroalkyl-substituted allylic alcohols are readily and selectively oxidized at the hydroxyl group with the Swern or Dess-Martin reagents to give α,β-unsaturated ketones, and on treatment with m-chloroperbenzoic acid or tert-butyl hydroperoxide they are oxidized to the corresponding epoxyalcohols. The latter are oxidized by Swern or Dess-Martin reagents at the hydroxyl group to α,β-epoxyketones, which form hydrates stable under the conditions of isolation.