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Anodic fluorination of azobenzene

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Abstract

Electrolysis of azobenzene (I) in the system of Et4NF · 3HF, MeCN results in predominant fluorination of the products of polymerization of I formed in the course of electrolysis. Also, m-fluoroazobenzene (II) and o-fluoroazobenzene (III) (II: III = 4: 1) were obtained with a low yield. Anomalously high content of m-isomer II is probably related to redistribution of localization of electron-deficient centers in cation-radical I as a result of its protonation by acidic electrolyte.

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References

  1. Domijan, J.D. and Ludman, C.J., McCarron, E.M., O’Malley, R.F., Roman, V.J, Inorg. Chem., 1969, vol. 8, no. 7, p. 1534.

    Article  CAS  Google Scholar 

  2. Rozhkov, I.N., Bukhtiyarov, A.V., Kuleshova, N.D., and Knunyants, I.L., Dokl. AN SSSR, 1970, vol. 193, p. 1322.

    CAS  Google Scholar 

  3. Knunyants, I.L., Rozhkov, I.N., Bukhtiyarov, A.V., Gol’din, M.M., and Kudryavtsev, R.V., Izv. Akad. Nauk SSSR, Ser. Khim., 1972, no. 5, p. 1207.

  4. Rozhkov, I.N., Bukhtiyarov, A.V., and Knunyants, I.L., Izv. Akad. Nauk SSSR, Ser. Khim., 1972, no. 5, p. 1130.

  5. Rozhkov, I.N., Usp. Khim., 1976, vol. 45, p. 1222.

    CAS  Google Scholar 

  6. Rozhkov, I.N., Bukhtiyarov, A.V., and Knunyants, I.L., Dokl. DAN SSSR, 1971, vol. 199, p. 369.

    CAS  Google Scholar 

  7. Eberson, L. and Nilsson, S., Abstracts of Faraday Soc. Meeting. Newcastle, 1968, no. 45.

  8. Harley, D.R. and Norman, R.O.C., J. Chem. Soc., 1964, p. 4860.

  9. Rozhkov, I.N., Doctoral (Chem.) Dissertation, Moscow: Institut elementoorgan. soed. (N.A. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences), 1977.

    Google Scholar 

  10. Shainyan, B.A., Danilevich, Yu.S., Grigor’eva, A.A., and Zhuravlev, Yu.A., Zhurn. Org. Khimii, 2004, vol. 40, no. 4, p. 544.

    Google Scholar 

  11. Nyberg, K., Acta Chem. Scand., 1971, vol. 25, pp. 534, 2499, 2770; 1973, vol. 27, p. 503.

    Article  CAS  Google Scholar 

  12. Soedineniya ftora (Fluorine Compounds), Ishikawa, N., Ed., Moscow: Mir, 1990.

    Google Scholar 

  13. Bruce, M., Goodall, B.L., and Stone, G.A., J. Chem. Soc., Dalton Trans., 1978, no. 6, p. 687.

  14. Puls-ml., Ch. and Oens, F., Nanotekhnologii (Nanotechnologies), Moscow: Tekhnosfera, 2007, pp. 302–303.

    Google Scholar 

  15. Andreades, S. and Zahnow, E.W., J. Am. Chem. Soc., 1969, vol. 91, p. 4181.

    Article  CAS  Google Scholar 

  16. Eberson, L., J. Am. Chem. Soc., 1967, vol. 89, no. 18, p. 4669.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia

    N. D. Kagramanov & S. R. Sterlin

  2. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Moscow, Russia

    V. A. Grinberg

Authors
  1. N. D. Kagramanov
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  2. S. R. Sterlin
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  3. V. A. Grinberg
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Correspondence to V. A. Grinberg.

Additional information

Original Russian Text © N.D. Kagramanov, S.R. Sterlin, V.A. Grinberg, 2009, published in Elektrokhimiya, 2009, Vol. 45, No. 11, pp. 1409–1412.

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Kagramanov, N.D., Sterlin, S.R. & Grinberg, V.A. Anodic fluorination of azobenzene. Russ J Electrochem 45, 1306–1309 (2009). https://doi.org/10.1134/S1023193509110135

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