Abstract
The kinetics of the oxidation of cyclopentanone with decaneperoxysulfonic acid at 291–323 K in CCl4 has been studied. The reaction is not autocatalytic, and its rate increases linearly with increases in the concentrations of each of the reagents. The addition of CF3COOH does not affect the reaction rate. The observed results are explained within a scheme which is a special case of the well-known Baeyer-Villiger reaction mechanism established for peroxycarboxylic acids. The effective rate constant of the process has been determined: logk (L mol−1 s−1)=(7.6±1.7) — (42.1±9.6)/θ, where θ=2.30RT kJ mol−1.
References
R. L. Safiullin, A. N. Volgarev, V. D. Komissarov, and G. A. Tolstikov,Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 2188 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990,39, 1998 (Engl. Transl.)].
R. L. Safiullin, A. N. Volgarev, G. Yu. Ishmuratov, M. P. Yakovleva, V. N. Odinokov, V. D. Komissarov, and G. A. Tolstikov,Dokl. Akad. Nauk SSSR, 1990,316, 640 [Dokl. Chem., 1990,316 (Engl. Transl.)].
R. L. Safiullin, A. N. Volgarev, N. I. Shishlov, and V. D. Komissarov,Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 1265 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990,39, 1136 (Engl. Transl.)].
A. J. Gordon and R. A. Ford,The Chemist's Companion, John Wiley & Sons, New York-London-Sydney-Toronto, 1972.
M. E. Hawthorne and W. D. Emmons,J. Am. Chem. Soc., 1958,80, 6393.
M. E. Hawthorne and W. D. Emmons,J. Am. Chem. Soc., 1958,80, 6398.
Y. Ogata and Y. Sawaki,J. Org. Chem., 1972,37, 2953.
G. Manivannan and P. Maruthamuthu,J. Chem. Soc., Perkin Trans. 2, 1986, 565.
B. W. Palmer and A. Fry,J. Am. Chem. Soc., 1970,92, 2580.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1827–1829, October, 1993.
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Safiullin, R.L., Volgarev, A.N. & Komissarov, V.D. The kinetics of the oxidation of cyclopentanone with decaneperoxysulfonic acid. Russ Chem Bull 42, 1751–1753 (1993). https://doi.org/10.1007/BF00697058
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DOI: https://doi.org/10.1007/BF00697058