Bridged ring systems. Part XIV. Preparation and reactivity of cis- and trans-3-allylcyclohexanol derivatives:— a potential π-route to the 3-bicyclo[3,3,1]nonyl cation

Abstract

The synthesis of 3-allylcyclohexanone (15) and the corresponding cis- and trans-3-allylcyclohexanols (13) and (14)(R = OH) from the bicyclo[3,3,1]nonane-1,3-diols (17) and (18)(R = OH) is described. The solvolytic behaviour of the corresponding esters (13) and (14)(R = OBs and OTs) has been examined, but no evidence for double-bond participation has been found either in rate measurements or product distribution.