The chemistry of aryllead(IV) tricarboxylates. Reaction with β-keto esters: a convenient route to α-arylated ketones

Abstract

Ethyl 2-oxocyclopentanecarboxylate (1a) and p-methoxyphenyllead triacetate (2a) react in chloroformcontaining pyridine to give ethyl 1-(p-methoxyphenyl)-2-oxocyclopentanecarboxylate (1b) in almost quantitative yield. This arylation reaction of β-keto esters has been examined with a variety of substrates and a number of aryllead triacetates and in all but one case in which the keto ester contained only one α-hydrogen the α-arylated β-keto ester was obtained in excellent yield. With ethyl acetoacetate both mono- and di-arylated products were obtained and yields were somewhat lower.