Reaction of phenylhydrazines with arenes in the presence of aluminium trichloride

Abstract

Phenylnitrenium ions are generated from phenylhydrazines by treatment with AlCl₃. Reaction of a phenylnitrenium ion with arenes results in both aromatic N-substitution and C-substitution. In contrast, an N-methylphenylnitrenium ion undergoes exclusively aromatic C-substitution. Reaction of a phenylnitrenium ion with arenes present only in slight excess produces anilinated products in moderate to good yields.