1,3-Dipolar cycloaddition of 3-imidazoline-3-oxide nitroxyl radical to dipolarophiles containing carbon-carbon double bonds

  • V. V. Martin
  • L. B. Volodarskii
  • M. A. Voinov
  • T. A. Berezina
  • T. F. Lelyukh
Organic Chemistry

Conclusions

  1. 1.

    Derivatives of 3-imidazoline-3-oxide react with dipolarophiles containing a C=C bond to form perhydroimidazo[1,5-b]isoxazoles. The reaction proceeds regio- and stereospecifically with the formation of 5-substituted isoxazolidines via a less hindered transition state.

     
  2. 2.

    The paramagnetic heterocyclic aldonitron, 2,2,5,5-tetramethyl-3-imidazoline-3-oxide-1-oxyl, can be used as a spin tracer for compounds containing a C=C bond.

     

Keywords

Transition State Double Bond Nitroxyl Isoxazoles Isoxazolidines 

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Copyright information

© Plenum Publishing Corporation 1989

Authors and Affiliations

  • V. V. Martin
    • 1
    • 2
  • L. B. Volodarskii
    • 1
    • 2
  • M. A. Voinov
    • 1
    • 2
  • T. A. Berezina
    • 1
    • 2
  • T. F. Lelyukh
    • 1
    • 2
  1. 1.Novosibirsk Institute of Organic Chemistry, Siberian BranchAcademy of Sciences of the USSRUSSR
  2. 2.Lenin Komsomol Novosibirsk State UniversityUSSR

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