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Asymmetric nitrogen. 71. Geminal systems. 45. N-halooxaziridines

  • S. V. Varlamov
  • G. V. Shustov
  • A. Yu. Shibaev
  • Yu. V. Puzanov
  • I. I. Chervin
  • R. G. Kostyanovskii
Organic Chemistry
  • 51 Downloads

Conclusions

  1. 1.

    We have synthesized for the first time N-chloro- and N-bromooxaziridines: a new type of geminal O-N-Hal system with high configurational stability of the N atom.

     
  2. 2.

    The halogen atom in N-halooxaziridines does not display anionic mobility. These compounds do not react with weak nucleophiles. But with strong nucleophiles, opening of the oxaziridine ring occurs along the N-O bond as a result of attack at the N atom.

     
  3. 3.

    Rearrangement of 2-chloro-3,3-di-tert-butyloxaziridine to the corresponding α-chloronitrosoalkane occurs as an intramolecular N→C migration of the Cl atom, with opening of the ring along the C-O bond.

     

Keywords

Nitrogen Migration Halogen Halogen Atom Configurational Stability 
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 1989

Authors and Affiliations

  • S. V. Varlamov
    • 1
  • G. V. Shustov
    • 1
  • A. Yu. Shibaev
    • 1
  • Yu. V. Puzanov
    • 1
  • I. I. Chervin
    • 1
  • R. G. Kostyanovskii
    • 1
  1. 1.N. N. Semenov Institute of Chemical PhysicsAcademy of Sciences of the USSRMoscow

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