Preparation of some allylic sulphones; base-catalysed isomerisation and deuteriation of cyclohex-2-enyl p-tolyl sulphones

Abstract

A summary of the methods used in the preparation of a range of allylic sulphones is given. In the case of the conformationally biased sulphones (5) and (6) stereospecific preparation from the cis- and trans-5-t-butylcyclohex-2-en-1-ols was achieved by rearrangement of the respective sulphenate esters, which occurred with high diastereoselectivity, followed by oxidation of the resulting sulphoxides. Base-catalysed equilibration and deuteriation studies on the six-membered cyclic allylic sulphones have been carried out.