Preparation of trans,trans,trans,cis- and trans,trans,trans,trans- tricyclo[7.3.1.05,13]tridecan-3-ols and acetolysis of the corresponding toluene-p-sulphonates

Abstract

The epimeric trans,trans,trans-tricyclo[7.3.1.0^5,13]tridecan-3-ols and their corresponding toluene-p-sulphonates have been produced in the first stereospecific general synthesis of this all-trans-carbocyclic system of fused cyclohexane rings; both toluene-p-sulphonates are less reactive than the t-butylcyclohexyl and trans-β-decalyl analogues (but not by large factors), but their epimeric rate ratio is the same and rates and the axial:equatorial epimeric rate ratios of these cyclohexyl toluene-p-sulphonates which are undistorted in their conformational ground states are much lower than for bridged cyclohexyl analogues.