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

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

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.

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Authors and Affiliations

  1. Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, USSR

    V. V. Martin, L. B. Volodarskii, M. A. Voinov, T. A. Berezina & T. F. Lelyukh

  2. Lenin Komsomol Novosibirsk State University, USSR

    V. V. Martin, L. B. Volodarskii, M. A. Voinov, T. A. Berezina & T. F. Lelyukh

Authors
  1. V. V. Martin
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  2. L. B. Volodarskii
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  3. M. A. Voinov
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  4. T. A. Berezina
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  5. T. F. Lelyukh
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1875–1882, August, 1988.

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Martin, V.V., Volodarskii, L.B., Voinov, M.A. et al. 1,3-Dipolar cycloaddition of 3-imidazoline-3-oxide nitroxyl radical to dipolarophiles containing carbon-carbon double bonds. Russ Chem Bull 37, 1677–1683 (1988). https://doi.org/10.1007/BF00961121

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  • DOI: https://doi.org/10.1007/BF00961121

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