Chemistry of Heterocyclic Compounds

, Volume 27, Issue 1, pp 96–102 | Cite as

Reactions of dimethyl 2-methoxyisoxazolidine-3,3-dicarboxylate catalyzed by Lewis acids

  • V. F. Rudchenko
  • V. N. Voznesenskii
  • R. G. Kostyanovskii
Article

Abstract

Evidence is presented for a synchronous mechanism of the acid-catalyzed 1,2-rearrangement of 2-methoxy-isoxazolidine-2,3-dicarboxylic acid ester with migration of the ester group to the N atom. It was shown that the reaction is suppressed in the presence of an external nucleophile or a reducing agent. The regularities found were used to explain the transformations of bicyclic systems with an -ONO-fragment.

Keywords

Ester Migration Organic Chemistry Dimethyl Acid Ester 

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Copyright information

© Plenum Publishing Corporation 1991

Authors and Affiliations

  • V. F. Rudchenko
    • 1
  • V. N. Voznesenskii
    • 1
  • R. G. Kostyanovskii
    • 1
  1. 1.N. N. Semenov Institute of Chemical PhysicsAcademy of Sciences of the USSRMoscow

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