Reactions of lead tetra-acetate. Part XI. The oxidation of styrene

Abstract

Styrene reacts with lead tetra-acetate to give at least four products, PhCH(OAc)Et, PhCH(OAc)·CH₂OAc, PhCH₂·CH(OAc)₂, and PhCHO. The relative yields of the first three are strongly dependent on the conditions of the reaction. A systematic study of these variations, together with kinetic evidence, has shown that the first product results from a radical-chain reaction and the third from a heterolytic process; the 1,2-diacetate is probably formed by two concurrent reactions of, respectively, homolytic type.