Reactions of lead(IV). Part XXVII. Oxidative rearrangement of styrene and related compounds to aldehydes or ketones in the presence of trifluoroacetic acid

Abstract

Aryl-conjugated olefins can undergo oxidative rearrangement to carbonyl compounds when treated with lead tetra-acetate in trifluoroacetic acid at room temperature. Excellent yields of arylacetaldehydes are obtained from styrene and some ring-substituted derivatives, but there are limitations to the synthetic utility of the method for other aryl-conjugated olefins.