Situselective α′-acetoxylation of some α,β-enones by manganic acetate oxidation

Abstract

Heating 5,5-dimethylcyclohex-2-en-1-one, 1, with manganic acetate in acetic acid yields 6-acetoxy-5,5-dimethylcyclohex-2-en-1-one, 2, as the only isolated product. Reaction of 3-methylcyclohex-2-en-1-one (3) or (+)-pulegone (5) under similar conditions yields the analogous 6-acetoxy-3-methylcyclohex-2-en-1-one (4) and cis- (6) and trans-2-acetoxypulegone (7) respectively.