The reaction of β-hydroxychalcone with lead tetraacetate gave benzil. The reaction of 4,4′-dimethoxy-β-hydroxychalcone gave 2-acetoxy-1,3-di(p-methoxyphenyl)propan-1,3-dione and 4,4′-dimethoxybenzil. The reactions of 2-acetoxy-1,3-diarylpropan-1,3-diones yielded 2,2-diacetoxy-1,3-diarylpropan-1,3-diones and benzils respectively. The formation of the benzils from β-hydroxychalcones and 2-acetoxy-1,3-diarylpropan-1,3-diones has been shown to involve 1,2-aryl and 1,2-aroyl migration respectively by studies of the oxidations of 14C-labelled compounds.
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Kurosawa et al. (1974) studied this question.
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