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Russian Chemical Bulletin

, Volume 56, Issue 11, pp 2239–2246 | Cite as

Selective mono-and diamination of polyfluorinated benzenes and pyridines with liquid ammonia

  • T. A. Vaganova
  • S. Z. Kusov
  • V. I. Rodionov
  • I. K. Shundrina
  • E. V. MalykhinEmail author
Article

Abstract

Amination of pentafluoropyridine, 2,3,5,6-tetrafluoropyridine, 4-chlorotetrafluoropyridine, 3,5-dichlorotrifluoropyridine, octafluorotoluene, α,α,α,2,3,5,6-heptafluorotoluene, decafluoro-m-xylene, decafluorobiphenyl, hexafluorobenzene, and pentafluorobenzene with liquid ammonia was investigated. Bis-aminodefluorination temperatures for the majority of substrates were shown to exceed significantly the corresponding temperatures of monoaminodefluorination. The optimal conditions for selective preparation of mono-and diaminopolyfluoro(het)arenes were elucidated. An efficient method for isolation of particular polyfluorophenylenediamines from product mixtures formed in nonselective reactions of pentafluorobenzene and hexafluorobenzene with aqueous ammonia based on complexation with a crown ether is proposed.

Key words

organofluorine compounds ammonia aminodefluorination polyfluorodiaminopyridines polyfluorophenylenediamines nucleophilic substitution 

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Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • T. A. Vaganova
    • 1
  • S. Z. Kusov
    • 1
  • V. I. Rodionov
    • 1
  • I. K. Shundrina
    • 1
  • E. V. Malykhin
    • 1
    • 2
    Email author
  1. 1.N. N. Vorozhtsov Novosibirsk Institute of Organic ChemistrySiberian Branch of the Russian Academy of SciencesNovosibirskRussian Federation
  2. 2.Novosibirsk State UniversityNovosibirskRussian Federation

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