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Treatment of N-benzylaziridine (1) with (aqua)xCu 2+ yields tetrabenzylcyclen 3 by a metal- assisted heterolytic (HETERO) pathway. Conversely, 1 is oxidised by the batho2Cu II ion (batho: 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline disulfonate) to afford benzaldehyde, dibenzylpiperazine 2 and 3, according to an electron-transfer mechanism (ET). Actually, evidence is presented for a competition between the ET and HETERO routes leading to 3. This competition is modulated by the pH of the solution, and experimental conditions are found where the contribution of the ET route unambiguously prevails.

Electron transfer vs. heterolytic reactions. Behaviour of N-benzyl aziridine towards (aqua)xCuII and batho2CuII ions