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Chemistry of Heterocyclic Compounds

, Volume 22, Issue 10, pp 1076–1079 | Cite as

Isomerization of 5-acyl-6-halo-1,6-diazabicyclo[3.1.0]hexanes, a case of inversion rather than 1,2-acyl migration

  • G. V. Shustov
  • S. N. Denisenko
  • I. I. Chervin
  • A. B. Zolotoi
  • O. A. D'yachenko
  • S. V. Konovalikhin
  • G. V. Shilov
  • L. O. Atovmyan
  • R. G. Kostyanovskii
Article

Abstract

X-ray diffraction structural analysis and 13C and 15N NMR spectroscopy were used to establish that the final product of the halogenation of 5-acyl-1,6-diazabicyclo[3.1.0]hexane is the exo-6-halo derivative. Thus, the observed transformation of the initially formed endo-N-chloro isomer is an inversion and not 1,2-acyl migration as previously proposed.

Keywords

Spectroscopy Migration Organic Chemistry Hexane Structural Analysis 
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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Copyright information

© Plenum Publishing Corporation 1987

Authors and Affiliations

  • G. V. Shustov
    • 1
  • S. N. Denisenko
    • 1
  • I. I. Chervin
    • 1
  • A. B. Zolotoi
    • 1
  • O. A. D'yachenko
    • 1
  • S. V. Konovalikhin
    • 1
  • G. V. Shilov
    • 1
  • L. O. Atovmyan
    • 1
  • R. G. Kostyanovskii
    • 1
  1. 1.Branch of the Institute of Chemical PhysicsAcademy of Sciences of the USSRChernogolovka

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