Hydrolysis of fluoroalkyl-containing Β-aminovinyl ketones

  • L. N. Bazhenova
  • V. I. Filyakova
  • V. E. Kirichenko
  • K. I. Pashkevich
Organic Chemistry


The kinetics of hydrolysis of fluoroalkyl-containing Β-aminovinyl ketones R1C(O)CHC(NHR3)R2, in which the substituents CF3 and HCF2CF2 are in the ketone (R1) or enamine parts of the molecule (R2), was studied. In acid (pH < 5) and alkaline (pH > 10) media, they hydrolyze with the formation of the corresponding amines and Β-diketones. In an alkaline medium, the Β-diketones undergo cleavage to fluorinated acids and methyl ketones. The rate constants of hydrolysis in an acid medium change within a range of four orders, depending on the nature of the substituents. The presence of a fluoroalkyl group at the enamine reaction center increases the hydrolysis rate. In an alkaline medium, the rate constants vary within one order.


Methyl Hydrolysis Ketone Reaction Center Acid Medium 
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Literature cited

  1. 1.
    Ya. F. Freimanis, Chemistry of Enamino Ketones, Enamino Imines, and Enamino Thiones [in Russian], Zinatne, Riga (1974).Google Scholar
  2. 2.
    J. V. Greenhill, Chem. Soc. Rev.,6, No. 3, 277 (1977).Google Scholar
  3. 3.
    D. N. Sokolov, Gas Chromatography of Volatile Metal Complexes [in Russian], Nauka, Moscow (1981).Google Scholar
  4. 4.
    D. N. Sokolov, Usp. Khim.,57, No. 10, 1670 (1988).Google Scholar
  5. 5.
    L. N. Bazhenova, Dissertation, Chemical Sciences, Inst. Khim. Ural Otd., Akad. Nauk SSSR, Sverdlovsk (1985).Google Scholar
  6. 6.
    J. Kovalec, Said-El-Bahey, and V. Sterba, Collect. Czech. Chem. Commun.,43, No. 10, 2732 (1978).Google Scholar
  7. 7.
    J. K. Coword and T. C. Bruice, J. Am. Chem. Soc.,91, No. 19, 5329 (1969).Google Scholar
  8. 8.
    J. P. Guthril and F. Jordan, J. Am. Chem. Soc.,94, No. 26, 9132 (1972).Google Scholar
  9. 9.
    J. Kovalek, J. Panchartek, T. Potesil, et al., Collect. Czech. Chem, Commun.,51, No. 3, 677 (1986).Google Scholar
  10. 10.
    S. S. Kiselev, M. K. Polievktov, and V. G. Granik, Khim. Geterotsikl. Soedin., No. 12, 1678 (1979).Google Scholar
  11. 11.
    K. I. Pashkevich, V. I. Filyakova, Yu. N. Sheinker, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2087 (1979).Google Scholar
  12. 12.
    K. I. Pashkevich and A. Ya. Aizikovich, Dokl. Akad. Nauk SSSR,244, No. 3, 618 (1979).Google Scholar
  13. 13.
    V. I. Saloutin, K. I. Pashkevich, and I. Ya. Postovskii, Zh. Vses. Khim. Ova,21, No. 2, 238 (1976).Google Scholar
  14. 14.
    A. Lovelace, D. Roach, and U. Postelnek, Aliphatic Fluorine-Containing Compounds [Russian translation], IL, Moscow (1961).Google Scholar
  15. 15.
    N. M. émanuél' and D. T. Knorre, Course in Chemical Kinetics [in Russian], Vysshaya Shkola, Moscow (1969).Google Scholar

Copyright information

© Plenum Publishing Corporation 1991

Authors and Affiliations

  • L. N. Bazhenova
    • 1
  • V. I. Filyakova
    • 1
  • V. E. Kirichenko
    • 1
  • K. I. Pashkevich
    • 1
  1. 1.Department of Fine Organic Synthesis, Institute of Chemistry, Bashkir Scientific Center, Urals BranchAcademy of Sciences of the USSRSverdlovsk

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