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Russian Chemical Bulletin

, Volume 56, Issue 7, pp 1394–1401 | Cite as

Synthesis and structures of tris(pentafluorophenyl)silylamines

  • V. V. Levin
  • A. D. Dilman
  • A. A. Korlyukov
  • P. A. Belyakov
  • M. I. Struchkova
  • M. Yu. Antipin
  • V. A. Tartakovsky
Article

Abstract

Tris(pentafluorophenyl)silylamines were synthesized by silylation of amines and imines with (C6F5)3SiCl or (C6F5)3SiOTf in the presence of triethylamine. The crystal structures of the (C6F5)3SiN(H)CH2Ph and (C6F5)3SiN(CH=CMe2)CH2Ph compounds were studied by X-ray diffraction. The crystal packings were analyzed by quantum chemical calculations in terms of the density functional theory (PBE exchange-correlation functional).

Key words

amines imines silylation organosilicon compounds organofluorine compounds X-ray diffraction analysis quantum chemical calculations 

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References

  1. 1.
    A. D. Dilman, P. A. Belyakov, A. A. Korlyukov, and V. A. Tartakovsky, Tetrahedron Lett., 2004, 45, 3741.CrossRefGoogle Scholar
  2. 2.
    V. V. Levin, A. D. Dilman, P. A. Belyakov, A. A. Korlyukov, M. I. Struchkova, and V. A. Tartakovsky, Eur. J. Org. Chem., 2004, 5141.Google Scholar
  3. 3.
    A. D. Dilman, P. A. Belyakov, A. A. Korlyukov, M. I. Struchkova, and V. A. Tartakovsky, Org. Lett., 2005, 7, 2913.CrossRefGoogle Scholar
  4. 4.
    V. V. Levin, A. D. Dilman, P. A. Belyakov, A. A. Korlyukov, M. I. Struchkova, M. Y. Antipin, and V. A. Tartakovsky, Synthesis, 2006, 489.Google Scholar
  5. 5.
    A. D. Dilman, D. E. Arkhipov, A. A. Korlyukov, V. P. Ananikov, V. M. Danilenko, and V. A. Tartakovsky, J. Organomet. Chem., 2005, 690, 3680.CrossRefGoogle Scholar
  6. 6.
    A. D. Dilman, D. E. Arkhipov, P. A. Belyakov, M. I. Struchkova, and V. A. Tartakovsky, Izv. Akad. Nauk, Ser. Khim., 2006, 498 [Russ. Chem Bull., Int. Ed., 2006, 55, 517].Google Scholar
  7. 7.
    A. D. Dilman, V. V. Levin, P. A. Belyakov, M. I. Struchkova, and V. A. Tartakovsky, Synthesis, 2006, 447.Google Scholar
  8. 8.
    M. F. Lappert and J. Lynch, Chem. Commun., 1968, 750.Google Scholar
  9. 9.
    K. Ruhlandt-Senge, R. A. Bartlett, M. M. Olmstead, and P. P. Power, Angew. Chem., Int. Ed., 1993, 32, 425.CrossRefGoogle Scholar
  10. 10.
    R. A. Bartlett and P. P. Power, J. Am. Chem. Soc., 1987, 109, 6509.CrossRefGoogle Scholar
  11. 11.
    W. Clegg, U. Klingebiel, J. Neemann, G. M. Sheldrick, and N. Vater, Acta Crystallogr., Sect. B, 1981, 37, 987.CrossRefGoogle Scholar
  12. 12.
    B. Fredelake, C. Ebker, U. Klingebiel, M. Noltemeyer, and S. Schmatz, J. Fluorine Chem., 2004, 125, 1007.CrossRefGoogle Scholar
  13. 13.
    S. Kliem, U. Klingebiel, M. Noltemeyer, and S. Schmatz, J. Organomet. Chem., 2005, 690, 1100.CrossRefGoogle Scholar
  14. 14.
    D. Schmidt-Base and U. Klingebiel, Z. Naturforsch., B: Chem. Sci., 1989, 44, 395.Google Scholar
  15. 15.
    U. Herzog, G. Roewer, B. Ziemer, and B. Herrschaft, J. Organomet. Chem., 1997, 533, 73.CrossRefGoogle Scholar
  16. 16.
    R. S. Rowland and R. Taylor, Phys. Chem., 1996, 100, 7384.CrossRefGoogle Scholar
  17. 17.
    R. F. W. Bader, Atoms in Molecules. A Quantum Theory, Clarendron Press, Oxford, 1990.Google Scholar
  18. 18.
    A. A. Korlyukov, S. A. Pogozhikh, Yu. A. Ovchinnikov, K. A. Lyssenko, M. Yu. Antipin, A. G. Shipov, O. A. Zamyshlyaeva, E. P. Kramarova, V. V. Negrebetky, I. P. Yakovlev, and Yu. I. Baukov, J. Organomet. Chem., 2006, 691, 3962.CrossRefGoogle Scholar
  19. 19.
    K. A. Lyssenko, A. A. Korlyukov, D. G. Golovanov, S. Yu. Ketkov, and M. Yu. Antipin, J. Phys. Chem. A, 2006, 110, 6545.CrossRefGoogle Scholar
  20. 20.
    E. Espinosa, E. Molins, and C. Lecomte, Chem. Phys. Lett., 1998, 285, 170.CrossRefGoogle Scholar
  21. 21.
    B. W. Gung and J. C. Amicangelo, J. Org. Chem., 2006, 71, 9261.CrossRefGoogle Scholar
  22. 22.
    L. L. Shipman, A. W. Burgess, and H. A. Scheraga, J. Phys. Chem., 1976, 80, 52.CrossRefGoogle Scholar
  23. 23.
    G. Bianchetti, P. D. Croce, D. Pocar, and A. Vigevani, Gazz. Chim. Ital., 1967, 97, 289.Google Scholar
  24. 24.
    H.-J. Frohn, A. Lewin, and V. V. Bardin, J. Organomet. Chem., 1998, 568, 233.CrossRefGoogle Scholar
  25. 25.
    G. Kresse and J. Hafner, Phys. Rev. B, 1993, 47, RC558.CrossRefGoogle Scholar
  26. 26.
    G. Kresse, Ph. D. Thesis, Technische Universität Wien, Wien, 1993.Google Scholar
  27. 27.
    G. Kresse and J. Furthmuller, Comput. Mat. Sci., 1996, 6, 15.CrossRefGoogle Scholar
  28. 28.
    G. Kresse and J. Furthmuller, Phys. Rev. B, 1996, 54, 11169.CrossRefGoogle Scholar
  29. 29.
    J. P. Perdew, S. Burke, and M. Ernzerhopf, Phys. Rev. Let., 1996, 77, 3865.CrossRefGoogle Scholar
  30. 30.
    G. Kresse and D. Joubert, Phys Rev. B, 1999, 59, 1758.CrossRefGoogle Scholar
  31. 31.
    X. Gonze, J.-M. Beuken, R. Caracas, F. Detraux, M. Fuchs, G.-M. Rignanese, L. Sindic, M. Verstraete, G. Zerah, F. Jollet, M. Torrent, A. Roy, M. Mikami, Ph. Ghosez, J.-Y. Raty, and D. C. Allan, Comput. Mat. Sci., 2002, 25, 478.CrossRefGoogle Scholar
  32. 32.
    D. N. Laikov, Chem. Phys. Lett., 1997, 281, 151.CrossRefGoogle Scholar
  33. 33.
    G. M. Sheldrick, SHELXTL-97, V5.10, Bruker AXS Inc., Madison, WI-53719, USA, 1997.Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • V. V. Levin
    • 1
  • A. D. Dilman
    • 1
  • A. A. Korlyukov
    • 2
  • P. A. Belyakov
    • 1
  • M. I. Struchkova
    • 1
  • M. Yu. Antipin
    • 2
  • V. A. Tartakovsky
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation
  2. 2.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation

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