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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
Article

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.

Keywords

Sodium Ammonia Organic Chemistry Nitrile Styrene 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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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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