ChemInform Abstract: DIAZOTIZATION OF AROMATIC PRIMARY AMINES OF WEAK BASICITY. II. REDUCTION OF ARENEDIAZONIUM SALTS WITH ALKYLBENZENE DERIVATIVES

The diazonio group of arenediazonium salts derived from weakly basic amines were efficiently substituted by hydrogen with alkylbenzenes in sulfuric acid. Several types of evidence, including kinetic results and experiments to trap an intermediate, indicated that the reduction occurs via an aryl radical intermediate. In the reduction with toluene, analyses of by-products suggested a radical chain mechanism, which would involve a propagation cycle caused by electron transfer from the benzyl radical to the diazonio group.