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.
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