Abstract
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.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1629–1638, December, 1974.
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Schmitz, E., Janisch, K. Epimination of olefins by means of 3,3-pentamethyleneoxaziridine — A one-step synthesis of aziridines. Chem Heterocycl Compd 10, 1432–1439 (1974). https://doi.org/10.1007/BF00474323
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DOI: https://doi.org/10.1007/BF00474323