Reactions of lead(IV). Part XXII. Radical-initiated oxidation of anisole

Abstract

The oxidation of anisole by lead tetra-acetate can occur by a radical-chain mechanism which leads to methylation, acetoxylation, and acetoxymethylation of the ring-carbon atoms and acetoxylation of the side-chain. The relative yields of the products vary markedly with the conditions, and especially with the addition of acetic acid; the causes of the variations are discussed. The radical-initiated reactions of anisole with lead tetrapropionate and of benzene with lead tetra-acetate are also reported.