SELECTIVE REACTIONS OF THIOLATE ANIONS WITH 4-HYDROXY-<i>E</i>-2-ALKENOIC ESTERS OR 4-METHANESULFONYLOXY-<i>E</i>-2-ALKENOIC ESTERS. SYNTHESIS OF 2-ALKEN-4-OLIDES (Δα,β-BUTENOLIDES) AND <i>E</i>,<i>E</i>-2,4-ALKADIENOIC ESTERS

Abstract

Abstract Methyl 4-hydroxy-E-2-alkenoates prepared from aldehydes in one step, undergo the Michael reactions with thiolate anions to give 4-alkanolide derivatives, which are converted into 2-alken-4-olides. Methyl 4-methanesulfonyloxy-E-2-alkenoates undergo the substitution reactions, and subsequent treatments give methyl E,E-2,4-alkadienoates.