The oxidative rearrangement of olefins by thallium(III) acetate. Part I. Oxidative rearrangement of chalcones

Abstract

The oxidation of 4-methoxychalcone (VIII) with methanolic thallium(III) acetate gives 3,3-dimethoxy-2-p-methoxyphenyl-1-phenylpropan-1-one (X). The reaction has been shown to involve a 1,2-aryl migration by a study of the oxidation of 4-methoxy[α-¹⁴C]chalcone and this mode of rearrangement contrasts with the 1,2-aroyl migration which had previously been observed in the boron trifluoride-catalysed rearrangement of chalcone epoxides.