Reactions of palladium(II) with organic compounds. Part 5. Effect of reaction conditions upon products of oxidation of α-methylstyrene

Abstract

The effects upon product distribution of varying the temperature, time of reaction, and reagent concentrations have been investigated in the oxidation of α-methylstyrene by palladium (II) acetate. Two reaction pathways have been identified. A π-allylic organopalladium compound decomposes slowly in a process catalysed by excess of the alkene to give 2-phenylprop-2-enyl acetate. The second reaction leads to competitive formation of enolic acetates and oxidative dimers but the organopalladium species involved has not been unambiguously identified. The addition of sodium acetate to the reaction, contrary to earlier reports, has only a marginal effect upon the distribution of products.