The dianion of benzyl phenyl sulphone. A general method for obtaining αβ-unsaturated phenyl sulphones from aldehydes and ketones

Abstract

The reaction between αα-dimetallo-derivatives of benzyl phenyl sulphone and carbonyl compounds has been shown to give αβ-unsaturated phenyl sulphones (IV), in yields strongly dependent upon the nature of the metal. Good yields have been obtained from saturated aliphatic and aromatic aldehydes and ketones, including αβ-unsaturated carbonyl compounds. The stereochemistry of the reaction has been studied. In the case of benzaldehyde and p-chlorobenzaldehyde only the Z-isomer was isolated; in the other cases a ca. 1 : 1 mixture of Z- and E-isomers was obtained.