Abstract
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.
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Literature cited
Ya. F. Freimanis, Chemistry of Enamino Ketones, Enamino Imines, and Enamino Thiones [in Russian], Zinatne, Riga (1974).
J. V. Greenhill, Chem. Soc. Rev.,6, No. 3, 277 (1977).
D. N. Sokolov, Gas Chromatography of Volatile Metal Complexes [in Russian], Nauka, Moscow (1981).
D. N. Sokolov, Usp. Khim.,57, No. 10, 1670 (1988).
L. N. Bazhenova, Dissertation, Chemical Sciences, Inst. Khim. Ural Otd., Akad. Nauk SSSR, Sverdlovsk (1985).
J. Kovalec, Said-El-Bahey, and V. Sterba, Collect. Czech. Chem. Commun.,43, No. 10, 2732 (1978).
J. K. Coword and T. C. Bruice, J. Am. Chem. Soc.,91, No. 19, 5329 (1969).
J. P. Guthril and F. Jordan, J. Am. Chem. Soc.,94, No. 26, 9132 (1972).
J. Kovalek, J. Panchartek, T. Potesil, et al., Collect. Czech. Chem, Commun.,51, No. 3, 677 (1986).
S. S. Kiselev, M. K. Polievktov, and V. G. Granik, Khim. Geterotsikl. Soedin., No. 12, 1678 (1979).
K. I. Pashkevich, V. I. Filyakova, Yu. N. Sheinker, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2087 (1979).
K. I. Pashkevich and A. Ya. Aizikovich, Dokl. Akad. Nauk SSSR,244, No. 3, 618 (1979).
V. I. Saloutin, K. I. Pashkevich, and I. Ya. Postovskii, Zh. Vses. Khim. Ova,21, No. 2, 238 (1976).
A. Lovelace, D. Roach, and U. Postelnek, Aliphatic Fluorine-Containing Compounds [Russian translation], IL, Moscow (1961).
N. M. émanuél' and D. T. Knorre, Course in Chemical Kinetics [in Russian], Vysshaya Shkola, Moscow (1969).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 664–669, March, 1991.
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Bazhenova, L.N., Filyakova, V.I., Kirichenko, V.E. et al. Hydrolysis of fluoroalkyl-containing Β-aminovinyl ketones. Russ Chem Bull 40, 581–585 (1991). https://doi.org/10.1007/BF00957999
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DOI: https://doi.org/10.1007/BF00957999