The different behaviour of cyclohexanones and their enamines in the reaction with methyl (E)- and (Z)-styryl sulphone

Abstract

Methyl(E)- and (Z)-styryl sulphone react with 4-t-butylcyclohexanone via Michael addition to furnish 8a-hydroxyperhydro-2-benzothiin 2,2-dioxides. Both isomeric unsaturated sulphones add at the carbon β to the SO₂ group and give predominantly the same trans-fused cyclic hydroxysulphone. The results of these reactions are compared with those obtained in the synthesis of the same cyclic products via the enamines.