Photochemical Eliminations Involving Zwitterionic Intermediates Generated via Electrocyclic Ring Closure of Benzothiophene Carboxanilides

Abstract

Leaving groups such as carboxylate, thiolate, and phenolate are expelled via zwitterionic intermediates produced upon photochemical electrocyclic ring closure of benzothiophene carboxanilides in the triplet excited state. Chemical yields generally exceed 90%, while quantum yields vary with basicity of the released leaving group.