Studies with Bicyclo[2,2,2]octenes. V. The behaviour of a series of Bicyclo[2,2,2]octenyl carbinols in acidified methanol

Abstract

A detailed account of the synthesis of three related bicyclo[2,2,2]octenyl carbinols (3),(4) and (5) and their behaviour in acidified methanol is presented. Seventeen different compounds which are intermediates of final stable end products have been isolated and characterized. In each case the products of acid-catalysed isomerization can be explained by postulating rearrangements involving stabilized carbonium ions.