Decomposition of meta and para alkylbenzenediazonium salts

Abstract

This work was undertaken for the purpose of further investigating the effects of alkyl substitution in aromatic compounds at positions remote from the point of substitution, and of learning how these effects vary with the nature of the alkyl group. Previous work in this field has led to no clear-cut explanations, and virtually no work has been done with meta alkyl substituents. The two series of compounds chosen for study were the meta and the para alkylbenzenediazonium fluoborates. The reactions of these substances with water to give the phenols was studied to give some additional information on the effect of alkyl groups. The ortho alkyl compounds were purposely omitted, because extraneous factors enter in, partly because of steric hindrance.