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Electrochemical Oxidation of 4-Hydroxyimino-2-pyrazolin-5-ones in Acetonitrile

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Abstract

Cyclic voltammetry and electrolysis in combination with ESR were used to study the electro- chemical oxidation of 1-R-4-hydroxyimino-3-methyl-2-pyrazolin-5-ones (R = H, C6H5, 4-BrC6H4, and 2-NO2-4-CF3C6H3) in acetonitrile on the background of 0.1 M Et4NClO4 on glassy carbon and platinum electrodes in the absence and in the presence of bases (pyridine, piperidine, tetraethylammonium hydroxide). With all the compounds, one-electron transfer gives rise to iminoxyl radicals (g 2.0045, aN 6 30.78-31.33, aN 1 1.87- 2.12). In alkaline medium the iminoxyl radical derived from 4-hydroxyimino-3-methyl-2-pyrazolin-5-one is unstable and oxidizes to 3-methyl-4-nitroso-1-pyrazolin-5-one. The oxidation potentials are much reduced with decreasing electron-acceptor power of the substituents and increasing basicity of the bases.

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REFERENCES

  1. Pozharskii, A.F., Teoreticheskie osnovy khimii geterotsiklov (Theoretical Fundamentals of Heterocyclic Chemistry), Moscow: Khimiya, 1985, p. 280.

    Google Scholar 

  2. The Theory of the Photographic Process, James, T.H., Ed., New York: Macmillan, 1977, 4th ed. Translated under the title Teoriya fotograficheskogo protsessa, Leningrad: Khimiya, 1980, p. 341.

    Google Scholar 

  3. Zolotov, Yu.A. and Kuz'min, N.M., Ekstraktsiya metallov atsilpirazolonami (Extraction of Metals with Acylpyrazolones), Moscow: Nauka, 1977, p. 140.

    Google Scholar 

  4. Kurbangalieva, A.R., Cand. Sci. (Chim.) Dissertation, Kazan, 1999.

  5. Caldararu, H., Caragheorgheopol, A., and Sahini, V.E., J. Magn. Reson., 1973, vol. 11, no. 3, pp. 335-343.

    Google Scholar 

  6. Wolff, L., Ber., 1904, vol. 37, no. 3, pp. 2827-2836.

    Google Scholar 

  7. Khaikin, M.S., Levkoev, I.I., and Kukhtin, V.A., Zh. Org. Khim., 1965, vol. 1, no. 1, p. 133.

    Google Scholar 

  8. Knorr, L., and Müller, E., Justus Liebigs Ann. Chim., 1903, vol. 328, pp. 62-77.

    Google Scholar 

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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center, Russian Academy of Sciences, Kazan, Tatarstan, Russia

    V. V. Yanilkin, A. V. Toropchina, V. I. Morozov, A. I. Movchan, L. P. Sysoeva, B. I. Buzykin & G. A. Chmutova

  2. Kazan State University, Kazan, Tatarstan, Russia

    V. V. Yanilkin, A. V. Toropchina, V. I. Morozov, A. I. Movchan, L. P. Sysoeva, B. I. Buzykin & G. A. Chmutova

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  1. V. V. Yanilkin
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  2. A. V. Toropchina
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  3. V. I. Morozov
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  4. A. I. Movchan
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  5. L. P. Sysoeva
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  6. B. I. Buzykin
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  7. G. A. Chmutova
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Yanilkin, V.V., Toropchina, A.V., Morozov, V.I. et al. Electrochemical Oxidation of 4-Hydroxyimino-2-pyrazolin-5-ones in Acetonitrile. Russian Journal of General Chemistry 71, 1620–1625 (2001). https://doi.org/10.1023/A:1013923624905

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  • DOI: https://doi.org/10.1023/A:1013923624905

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