Studies in the chemistry of benzo-bicyclic systems

The work described in this thesis is concerned with the major factors controlling the acid-catalysed rearrangements of methyl-substituted 1-methoxybenzobarrelenes. A short summary is presented in chapter one on the cycloaddition reactions of arynes with arenes, discussing the principle reactions and factors influencing the orientation of the 1,4-cycloaddition. Some of the recent advances in the chemistry of carbocations involved in the secondary rearrangements of highly substituted benzobarrelenes have been discussed. Chapter two discusses the reactions of tetrahalogenobenzyne with mono- and polysubstituted anisoles (e.g. 2-methyl, 2,3-dimethyl and 2,3,5,6-tetramethyl etc.) which results in the formation of substituted tetrahalogenobenzobarrelenones and 1-methoxytetrahalogenobenzobarrelenes. A method for the preparation of 2,3-dimethoxytoluene in high yield has been presented. [Continues.]