Catalytic phosphorylation of polyfluoroalkanols 13. Some ammonium and phosphonium salts as phosphorylation catalysts

  • M. I. Kabachnik
  • L. S. Zakharov
  • I. Yu. Kudryavtsev
Organic Chemistry
Received:
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Abstract

It was shown that it is possible to use a series of ammonium and phosphonium salts as effective catalysts for the preparative synthesis of tris(polyfluoroalkyl) phosphates. The effect of the structure of substituted ammonium salts on their catalytic activity was studied in the phosphorylation of 1,1-dihydroperfluorobutanol by phosphorus oxychloride. It was determined that the reaction rate is affected not only by the solubility of the salt, but also by the nature of the ion pair and the steric access of the onium center for solvation by phosphoryl compounds.

Keywords

Phosphate Ammonium Phosphorus Catalytic Activity Phosphonium 
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Literature cited

  1. 1.
    L. S. Zakharov, V. V. Pisarenko, N. N. Godovikov, and M. I. Kabachnik, Izv. Akad. Nauk SSSR, Ser. Khim., No. 11, 2503 (1971).Google Scholar
  2. 2.
    I. Yu. Kudryavtsev, L. S. Zakharov, and M. I. Kabachnik, Izv. Akad. Nauk SSSR, Ser. Khim., No. 11, 2535 (1982).Google Scholar
  3. 3.
    D. F. Evans, J. A. Nadas, and S. M. A. Matesich, J. Phys. Chem.,75, No. 11, 1708 (1971).Google Scholar
  4. 4.
    M. Baaz and V. Gutmann, Monatsh. Chem.,90, No. 2, 256 (1959).Google Scholar
  5. 5.
    R. A. Lidin, L. L. Andreeva, and V. A. Molochko, Handbook of Inorganic Chemistry [in Russian], Khimiya, Moscow (1987), p. 60.Google Scholar
  6. 6.
    H. L. Klug and A. M. Pardee, Proc. S. Dakota Acad. Sci.,25, 48 (1945); Chem. Abstr.,40, No. 22, Abstract No. 69512 (1946).Google Scholar
  7. 7.
    W. H. Hunter and G. D. Byrkit, J. Am. Chem. Soc.,54, No. 5, 1948 (1932).Google Scholar
  8. 8.
    L. W. Jones and H. F. Whalen, J. Am. Chem. Soc.,47, No. 5, 1343 (1925).Google Scholar
  9. 9.
    W. E. Thompson and C. A. Kraus, J. Am. Chem. Soc.,59, No. 5, 1016 (1947).Google Scholar
  10. 10.
    K. D. McMichael and R. A. Clement, J. Org. Chem.,26, No. 2, 620 (1961).Google Scholar
  11. 11.
    J. Grimshaw and J. S. Ramsey, J. Chem. Soc. B, No. 1, 63 (1968).Google Scholar
  12. 12.
    G. Wittig and D. Wittenberg, Liebigs Ann. Chem.,606, 1 (1957).Google Scholar
  13. 13.
    D. É. Balode and A. Kh. Zitsmanis, Izv. Akad. Latv.SSR, Ser. Khim., No. 1, 71 (1976).Google Scholar
  14. 14.
    H. O. House and G. H. Rasmusson, J. Org. Chem.,26, No. 11, 4278 (1961).Google Scholar

Copyright information

© Plenum Publishing Corporation 1990

Authors and Affiliations

  • M. I. Kabachnik
    • 1
  • L. S. Zakharov
    • 1
  • I. Yu. Kudryavtsev
    • 1
  1. 1.A. N. Nesmeyanov Institute of Heteroorganic CompoundsAcademy of Sciences of the USSRMoscow

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