Synthesis and stereochemistry of substituted perhydro-2-thiaindan and 2-thiadecalin 2,2-dioxides

Abstract

The intramolecular cyclization in basic medium of 2-(α-methylsulphonylphenethyl)cyclohexanone (1) leads to three isomeric 1-benzyl-3a-hydroxyperhydro-2-thiaindan 2,2-dioxides (3), (4), and (5). Under the same conditions three isomeric 4-phenyl-8a-hydroxy-2-thiadecalin 2,2-dioxides (12), (13), and (14), are obtained from 2-α-(methylsulphonylmethyl)benzylcyclohexanone (10). The configurations of the products have been established by spectroscopic and chemical methods.