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Geminal systems. 18. Acid-catalyzed reactions of N-alkoxyisoxazolidines

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

Conclusions

  1. 1.

    Acid-catalyzed transformations, such as replacement of the N-methoxy group or splitting of MeNHCO2Me in an alcoholic medium, and 1,2-migration of the MeO2C group to the N atom, or irreversible splitting-addition of the MeO group in an inert medium, are characteristic of the derivatives of 2-methoxyisoxazolidine-3,3-dicarboxylic acid.

  2. 2.

    The selectivity of the cleavage of the heterocyclic rings containing the O-N-O structural fragment is subject to stereoelectronic control.

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Authors and Affiliations

  1. Institute of Chemical Physics, Academy of Sciences of the USSR, Moscow

    V. F. Rudchenko, V. G. Shtamburg, A. P. Pleshkova & R. G. Kostyanovskii

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  1. V. F. Rudchenko
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  2. V. G. Shtamburg
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  3. A. P. Pleshkova
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  4. R. G. Kostyanovskii
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Additional information

See [1] for Article 17.

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2549–2555, November, 1981.

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Rudchenko, V.F., Shtamburg, V.G., Pleshkova, A.P. et al. Geminal systems. 18. Acid-catalyzed reactions of N-alkoxyisoxazolidines. Russ Chem Bull 30, 2110–2116 (1981). https://doi.org/10.1007/BF01094640

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  • DOI: https://doi.org/10.1007/BF01094640

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