Chemistry of Heterocyclic Compounds

, Volume 10, Issue 12, pp 1432–1439 | Cite as

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

  • E. Schmitz
  • K. Janisch


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.


Sodium Ammonia Organic Chemistry Nitrile Styrene 
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Copyright information

© Plenum Publishing Corporation 1976

Authors and Affiliations

  • E. Schmitz
    • 1
  • K. Janisch
    • 1
  1. 1.Central Institute of Organic ChemistryAcademy of Sciences of the German Democratic RepublicBerlin-Adlershof

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