Epimination of olefins by means of 3,3-pentamethyleneoxaziridine — A one-step synthesis of aziridines

3,3-Pentamethyleneoxaziridine, which is readily obtained by treatment of cyclohexanone with ammonia and sodium hypochlorite or hydroxylamine-O-sulfonic acid, reacts with olefins with transfer of the NH group to give aziridines. Aziridines were obtained from styrene, ring- or side-chain-substituted styrenes, norbornene, and acrylonitrile in 20–70% yields. Cyclohexene is doubly aminated to give N-aminoaziridine. Nitriles are formed from phenylacetylene and diphenylacetylene as a result of rearrangement.