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Chemistry of Heterocyclic Compounds

, Volume 53, Issue 12, pp 1330–1334 | Cite as

Reactions of pyridin-2-ol, pyridin-3-ol, and pyridin-4-ol with pentafluoro- and pentachloropyridine

  • Reza Ranjbar-KarimiEmail author
  • Tayebeh Davodian
  • Hossein Mehrabi
Article
  • 78 Downloads

Reactions of pentafluoro- and pentachloropyridines with pyridin-2-ol, pyridin-3-ol, and pyridin-4-ol are reported. Pyridin-4-ol yields product of attack at the nitrogen atom, while pyridin-3-ol reacts at the oxygen atom. Pyridin-2-ol reacts as an ambident nucleophile, providing a mixture of products arising from attack at both the oxygen and the nitrogen atoms. The structures of compounds were confirmed by IR spectroscopy, 1H, 13C, and 19F NMR spectroscopy, as well as elemental analysis and X-ray crystallography.

Keywords

pentachloropyridine pentafluoropyridine pyridinol aromatic nucleophilic substitution chemoselectivity synthesis 

Notes

The authors wish to thank Vali-e-Asr University of Rafsanjan for partially funding this work.

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Reza Ranjbar-Karimi
    • 1
    Email author
  • Tayebeh Davodian
    • 1
  • Hossein Mehrabi
    • 1
  1. 1.Department of Chemistry, Faculty of ScienceVali-e-Asr UniversityRafsanjanIslamic Republic of Iran

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