Studies with Bicyclo[2,2.2]octenes. IV. Acid-catalysed fragmentation of Bicyclo[2,2,2]octenyl dialkyl carbinols to aromatic compounds

Abstract

Attempts to prepare the conjugated ester (1) by dehydration of the hydroxy ester (2) failed with a variety of acidic reagents, and the major product in each case was the aromatic ester (3). Similarly, the carbinols (13) and (14) rearranged to (15) under acidic conditions. In particular, the use of acidified methanol produced a variety of intermediates, eight of which were isolated by preparative gas chromatography. The mechanism of the rearrangement is discussed.