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Russian Chemical Bulletin

, Volume 46, Issue 7, pp 1291–1299 | Cite as

Sterically hindered inversion of nitrogen atoms in cyclic hydrazines:N,N′-dialkyl-1,3,4-oxadiazolidines; 1,3,4-thiadiazolidine; and 4,5-benzo-1,2,3,6-tetrahydropyridazine

  • R. G. Kostyanovsky
  • P. Rademacher
  • Yu. I. El'natanov
  • G. K. Kadorkina
  • G. A. Nikiforov
  • I. I. Chervin
  • S. V. Usachev
  • V. R. Kostyanovsky
Asymmetric Nitrogen

Abstract

N,N′-Diisopropyl-substituted 1,3,4-oxadiazolidine3c, 1,3,4-thiadiazolidine6, 4,5-benzo-1,2,3,6-tetrahydropyridazine8, and new 3,4-dialkyl-1,3,4-oxadiazolidines9–14 were synthesized and studied. The configurational stability of the N atoms does not change on going from compound3c to itsS-analog6 and decreases in the case of pyridazine8. 3,4-Di-tert-alkyl-1,3,4-oxadiazolidines3d and11–14 were found to be promising objectes for optical resolution.

Key words

N,N′-dialkyl-substituted 1,3,4-oxadiazolidines 1,3,4-thiadiazolidine 4,5-benzo-1,2,3,6-tetrahydropyridazine nitrogen inversion 113C NMR 

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Copyright information

© Plenum Publishing Corporation 1997

Authors and Affiliations

  • R. G. Kostyanovsky
    • 1
  • P. Rademacher
    • 2
  • Yu. I. El'natanov
    • 1
  • G. K. Kadorkina
    • 1
  • G. A. Nikiforov
    • 1
  • I. I. Chervin
    • 1
  • S. V. Usachev
    • 1
  • V. R. Kostyanovsky
    • 1
  1. 1.N. N. Semenov Institute of Chemical PhysicsRussian Academy of SciencesMoscowRussian Federation
  2. 2.Institute of Organic ChemistryUniversity of EssenGermany

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