Enol elimination reactions. Part III. The scope and limitations of eliminations involving enol sulphonates

Abstract

Elimination reactions of enol sulphonates have been further studied. The enol sulphonates of p-anisolyl-, 2-furoyl-, and 2-thenoyl-malonic esters readily gave the corresponding propiolic acids on treatment with base, whereas the enol sulphonates of o-, m-, and p-nitrobenzoylmalonic esters gave negligible yields. The enol sulphonates of cyclopropylcarbonylmalonate gave cyclopropylpropiolic acid, while those of trichloroacetylmalonate and fumaroylmalonate gave no acetylenic product. The enol sulphonates of tribenzoylmethane gave benzoylphenyl-acetylene.