Mild carbon–carbon bond cleavage of carbonyl compounds using pentafluoroiodobenzene bis(trifluoroacetate)

Abstract

Acetophenones, α-hydroxyacetophenones, deoxybenzoin, benzoin, and benzil are cleaved oxidatively with pentafluoroiodobenzene bis-(trifluoroacetate) in wet benzene at room temperature to give the corresponding benzoic acids; cyclohexanone and dimedone are cleaved to give the diacids adipic acid and 3,3-dimethylglutaric acid, respectively.