Reactivity of substituted benzoic acids and their complexes with 2,4,6-trinitrotoluene toward diphenyldiazomethane

Abstract

The reactions of 2,4-dihydroxybenzoic and 4-aminobenzoic acids with diphenyldiazomethane are accelerated in the presence of 2,4,6-trinitrotoluene as π-acceptor. The catalytic effect of the latter is determined by the formation of charge-transfer complexes with the acids, which facilitates proton abstraction and stabilizes the corresponding anions.