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Chemistry of Heterocyclic Compounds

, Volume 47, Issue 7, pp 817–825 | Cite as

Synthesis and structure of asymmetric 2,4,6-triazidopyridines

  • S. V. ChapyshevEmail author
  • D. V. Korchagin
  • G. V. Shilov
  • S. M. Aldoshin
Article

The reactions of 3-cyanotetrafluoropyridine and tetrachloro-3-trifluoromethylpyridine with sodium azide lead to the corresponding 2,4,6-triazido-5-cyano-3-fluoropyridine and 2,4,6-triazido-5-chloro-3-trifluoromethylpyridine. With the aid of comparative X-ray structural analysis of 2,4,6-triazido-5-cyano-3-fluoropyridine and its previously known 3-chloro-substituted derivative it was established that the geometric parameters and reactivity of the azide groups in the asymmetric 2,4,6-triazi-dopyridines depend not only on the position of these groups in the pyridine ring but also on their mutual orientation in space.

Keywords

azides pyridines high-energy materials nucleophilic substitution X-ray structural analysis 

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Copyright information

© Springer Science+Business Media, Inc. 2011

Authors and Affiliations

  • S. V. Chapyshev
    • 1
    Email author
  • D. V. Korchagin
    • 1
  • G. V. Shilov
    • 1
  • S. M. Aldoshin
    • 1
  1. 1.Institute of Problems of Chemical PhysicsRussian Academy of SciencesChernogolovkaRussia

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