Syntheses with carbanions derived from carbonyl-stabilized sulphonium ylides: a novel route to furan-3(2H)-ones

Abstract

The sulphonium αα′-dicarbonylmethylides (I) were acylated at the β-position in the presence of n-butyl-lithium or lithium di-isopropylamide. These acylated sulphonium ylides underwent thermal elimination of dimethyl sulphide to give alkyl- and aryl-substituted furan-3(2H)-ones (3-hydroxyfurans). The mechanism of furanone formation is discussed.