The chemistry of aryllead(IV) tricarboxylates. Reaction with enamines

Abstract

The treatment of 1-morpholinocyclopentene (la) with p-methoxyphenyllead triacetate (2a) in chloroform provides a simple high-yielding route to 2-(4-methoxyphenyl)cyclopentanone (3a). This arylation reaction of enamines has been investigated with a variety of substrates and a number of aryllead triacetates. The reaction has been found to be very sensitive to steric effects and is thus a useful synthetic method in a relatively small number of cases. Acetoxylation is a major competing reaction with those enamines of cyclic ketones which give a low to moderate yield of arylated product.