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Russian Journal of Organic Chemistry

, Volume 52, Issue 2, pp 200–205 | Cite as

Synthesis of chloropolyfluoroarenes from polyfluoroarenethiols and PCl5

  • P. V. Nikul’shin
  • А. M. Maksimov
  • V. Е. PlatonovEmail author
Article

Abstract

Replacement of the thiol group in polyfluoroarenethiols with chlorine was performed by treating with PCl5 as chlorinating agent. By heating in ampules at 200–220°C polyfluoro- and polyfluorochloroarenethiols with PCl5 mono- and dichloropolyfluoroarenes and also 1,2,4-trifluorotrichlorobenzene were synthesized. Dichloropolyfluoroarenes contain chlorine atoms in ortho- and para-positions.

Keywords

Thiol Chlorine Atom Pentafluorophenyl Triethyl Phosphite Sulfuryl Chloride 
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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References

  1. 1.
    Weiss, R.G. and Snyder, E.I., J. Chem. Soc. Chem. Commun., 1968, p. 1358.Google Scholar
  2. 2.
    Dagani, M.J., US Patent no. 3624159, 1971; Chem. Abstr., 1972, vol. 76, no. 46304z.Google Scholar
  3. 3.
    Cadogan, J.I.G. and Foster, W.R., J. Chem. Soc., 1961, p. 3071.Google Scholar
  4. 4.
    Clive, D.L.J. and Denyer, C.V., J. Chem. Soc., Chem. Commun., 1972, p. 773.Google Scholar
  5. 5.
    Iranpoor, N., Firouzabadi, H., and Aghapour, G., Synlett., 2001, p. 1176.Google Scholar
  6. 6.
    Still, I.W.J., Kutney, G.W., and McLean, D., J. Org. Chem., 1982, vol. 47, p. 560.CrossRefGoogle Scholar
  7. 7.
    Platonov, V.E., Maksimov, A.M., Dvornikova, K.V., and Nikul’shin, P.V., Russ J. Org. Chem., 2005, vol. 41, p. 1647.CrossRefGoogle Scholar
  8. 8.
    Nikul’shin, P.V., Maksimov, A.M., and Platonov, V.E., Russ. J. Appl. Chem., 2010, vol. 83, p. 1254.CrossRefGoogle Scholar
  9. 9.
    Reid, K.F., Properties and Reactions of Bonds in Organic Molecules, London: Longmans, Green & Co. Ltd., 1968.Google Scholar
  10. 10.
    Cotton, F.A. and Wilkinson, G., Advanced Inorganic Chemistry, New York: Intersci. Publ., a Division of John Wiley & Sons Inc., 1966.Google Scholar
  11. 11.
    Wyman, D.P., Wang, G.Y.C., and Freeman, W.R., J. Org. Chem., 1963, vol. 28, p. 3173.CrossRefGoogle Scholar
  12. 12.
    Ingold, K.U. and Roberts, B.P., Free-Radical Substitution Reactions, New York: Wiley-Intersci., a Division of John Wiley & Sons Inc., 1971.Google Scholar
  13. 13.
    Fischer, W. and Jüebermann, O., Z. Anorg. Chem., 1938, vol. 235, p. 337.CrossRefGoogle Scholar
  14. 14.
    De La Mare, P.B.D. and Bolton, R., Electrophilic Additions to Unsaturated Systems, Amsterdam: Elsevier, 1966.Google Scholar
  15. 15.
    Downs, A.J. and Adams, C.J., Compr. Inorg. Chem., 1973, vol. 2, p. 1144.Google Scholar
  16. 16.
    Smith, L.J.H., Comprehensive Organic Chemistry. The Synthesis and Reactions of Organic Compounds, Barton, D. and Ollis, W.D., Eds., Oxford: Pergamon Press, 1979, vol. 2, p. 1158.Google Scholar
  17. 17.
    Maksimov, A.M. and Platonov, V.E., Fluor. Notes, 1999, vol. 4. http://notes.fluorine1.ru/contents/history/1999/4_1999/index.html.Google Scholar
  18. 18.
    Nikul’shin, P.V., Maksimov, A.M., and Platonov, V.E., Russ. J. Org. Chem., 2012, vol. 48, p. 536.CrossRefGoogle Scholar
  19. 19.
    Van Wazer, J.R., Callis, C.F., Shoolery, J.N., and Jones, R.C., J. Am. Chem. Soc., 1956, vol. 78, p. 5715.CrossRefGoogle Scholar
  20. 20.
    http://eu.wiley.com/WileyCDA/WileyTitle/productCd-1118980883.html.Google Scholar
  21. 21.
    Hein, R.E. and McFarland, R.H., J. Am. Chem. Soc., 1952, vol. 74, p. 1856.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2016

Authors and Affiliations

  • P. V. Nikul’shin
    • 1
  • А. M. Maksimov
    • 1
  • V. Е. Platonov
    • 1
    Email author
  1. 1.Vorozhtsov Novosibirsk Institute of Organic ChemistrySiberian Branch of the Russian Academy of SciencesNovosibirskRussia

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