Aryne chemistry. Part XXVIII. Some further cycloaddition reactions of tetrahalogenobenzynes generated from tetrahalogenoanthranilic acids

Abstract

Tetrabromo- and tetraiodo-benzyne can be generated efficiently from the corresponding tetrahalogenoanthranilic acids, and undergo cycloaddition reactions in solution with aromatic substrates. Competition data have been compared with those obtained for tetrachloro- and tetrafluoro-benzyne. Certain substituted tetrabromobenzo-barrelenes are converted into naphthalene derivatives in the presence of 3-methylbutyl nitrite.