The chemistry of aryllead(IV) tricarboxylates. Reaction with α-hydroxymethylene ketones : a route to α-arylated ketones

Abstract

α-Hydroxymethylene ketones have been shown to react with aryllead triacetates in tetrahydrofuran containing pyridine to give α-aryl α-formyl ketones, unstable compounds, which were hydrolysed directly with alkali to α-aryl ketones. The procedure has been used to produce in good yield 2-(p-methoxyphenyl)cyclohexanone, 2-(p-tolyl)cyclohexanone and the corresponding derivatives of4-t-butylcyclohexanone, and 2α-(p-methoxypheny1)-5α-cholestan-3-one and 3β-hydroxy-16α-(pmethoxypheny1)-5α-androstan-17-one.