Reactions of lead tetra-acetate. Part X. Mechanism of oxidative rearrangement of two 3,3,3-triarylpropenes with lead tetra-acetate and in the Prévost reaction

Abstract

The reactions of the olefins Ph₂ArC·CHCH₂(Ar = Ph and p-anisyl) with lead tetra-acetate and with iodine in the presence of silver acetate have been studied and conclusions have been reached about the mechanisms of oxidation (which, in all cases, is accompanied by rearrangement). In particular, evidence is adduced that a carbonium ion is formed at each of two phases of the reaction with each reagent. The olefins Ph₂ArC·CMeCH₂(Ar = Ph and p-anisyl) are not oxidised by lead tetra-acetate under the same conditions, although evidence was obtained that the latter olefin forms a complex with the oxidant.