The Chemistry of Aryllead(IV) Tricarboxylates. Reaction with β-Diketones

Abstract

Dimedone (1) and p-methoxyphenyllead triacetate (2) react in chloroform containing pyridine at 40º to give 2,2-bis(p-methoxyphenyl)-5,5-dimethylcyclohexane-,3-dione (3) in high yield. This arylationreaction of β-diketones has been examined with 2-methylcyclohexane-1,3-dione, 2-methylcyclopentane-1,3-dione, acetylacetone and 2-acetyl-3,4-dihydronaphthalen-l(2H)-one, and in all cases synthetically useful yields of arylated products were obtained. The vinylogous β-diketone, 6β-acetylcholest-4-en-3-one, also underwent the reaction to give a mixture of 6β-acetyl-6α-(p-methoxypheny1)-cholest-4-en-3-one (21) and the corresponding 6β-aryl compound (22).