The work described in this thesis forms part of an attempt to understand some of the factors controlling the acid-catalysed rearrangements of 1-methoxybenzobarrelenes. A review is presented in chapter one of the important features of the rearrangement-chemistry of dibenzo- and benzo-barrelenes. The commonly observed interconversion of the bicyclo[2,2,2]octadien-2-yl and bicyclo[3,2,1]octadien-2-yl cations is discussed in detail and finally some of the extensive rearrangements of highly substituted benzobarrelenes are presented to illustrate the more subtle aspects of the rearrangements.