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Chemistry of Heterocyclic Compounds

, Volume 15, Issue 5, pp 484–488 | Cite as

2-Alkylisoxazolidine-3,3-dicarboxylic acid derivatives

  • A. V. Prosyanik
  • A. I. Mishchenko
  • N. L. Zaichenko
  • Ya. Z. Zorin
  • R. G. Kostyanovskii
  • V. I. Markov
Article
  • 30 Downloads

Abstract

1,3-Dipolar cycloaddition ofα,α-bis(alkoxycarbonyl)-N-alkylnitrones to olefins gave 2-alkylisoxazolidine-3,3-dicarboxylic acid esters, the yields of which are determined by the steric conditions and are virtually independent of the electronic effect of the substituents attached to the C=C bond of the dipolarophiles. The structures of the compounds obtained were established by analysis of the PMR spectra. The retention of the cis configuration of the substituents in the isoxazolidines obtained from maleic acid esters constitutes evidence for a one-step, four-center, concerted cycloaddition mechanism. The energy parameters for inversion of the nitrogen atom of dimethyl 2,5,5-trimethylisoxazolidine-5,5-dicarboxylate were measured.

Keywords

Nitrogen Ester Dimethyl Nitrogen Atom Acid Derivative 
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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Literature cited

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Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • A. V. Prosyanik
    • 1
    • 2
  • A. I. Mishchenko
    • 1
    • 2
  • N. L. Zaichenko
    • 1
    • 2
  • Ya. Z. Zorin
    • 1
    • 2
  • R. G. Kostyanovskii
    • 1
    • 2
  • V. I. Markov
    • 1
    • 2
  1. 1.F. É. Dzerzhinskii Dnepropetrovsk Institute of Chemical TechnologyDnepropetrovsk
  2. 2.Institute of Chemical PhysicsAcademy of Sciences of the USSRMoscow

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