The chemistry of aryllead tricarboxylates. Synthesis of some α-aryl α,β-unsaturated carbonyl compounds

Abstract

The treatment of 4-benzoyltetrahydrofuran-2,3-dione (2a) with 2 equiv. of phenyllead triacetate (3a) in chloroform gives 1,2-diphenylpropenone (4a) in excellent yield. This reaction has been investigated with a number of similar derivatives of tetrahydrofuran-2,3-dione and a number of aryllead triacetates. It has been found to be very sensitive to the nature of the substituent at C4, and it would appear to be limited to the synthesis of a-methylene carbonyl compounds since a 5-methyl substituent inhibits the reaction.