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Статья
2000

Step wise and dissociative mechanisms of the electron transfer in electrochemical reactions involving organosilicon compounds: Molecular-thermodynamic approach1


V. V. ZhuikovV. V. Zhuikov
Российский электрохимический журнал
https://doi.org/10.1007/BF02756895
Abstract / Full Text

Electrochemical reduction of organochlorosilanes and oxidation of hexaorganodisilanes may occur via dissociative and stepwise mechanisms, the choice between which is determined by the balance between fundamental structural parameters of elementoorganic molecules. The formation of radical anions of silyl-substituted chloromethane in the conditions of an electrochemical experiment is shown. The formation is due to α-silicon stabilization of the intermediate during the electron transfer. The role of conjugation and hyperconjugation in the organosilicon compounds’ reactivity is analyzed.

Author information
  • Kazan State University, ul. Lenina 18, Kazan, 420008, Tatarstan, RussiaV. V. Zhuikov
References
  1. Saveant, J.-M., inAdvances in Physical and Organic Chemistry, 1990, vol. 26, p. 2.
  2. Andrieux, C.P.,Pure Appl. Chem., 1994, vol. 66, p. 2445.
  3. Genies, E.M. and El Omar, A.F.,Electrochim. Acta, 1983, vol. 28, p. 541.
  4. Yoshida, J., inTopics in Current Chemistry, Berlin: Springer, 1994, p. 40.
  5. Zhuikov, V.V.,Usp. Khim., 1997, vol. 66, p. 564.
  6. Andrieux, C.P., Gallardo, I., Saveant, J.-M., and Su, K.B.,J. Am. Chem. Soc., 1986, vol. 108, p. 638.
  7. Andrieux, C.P., Le Gorande, A., and Saveant, J.-M.,J. Am. Chem. Soc., 1992, vol. 114, p. 6892.
  8. Saveant, J.M., inAdvances in Electron Transfer Chemistry, 1994, vol. 4, p. 53.
  9. Saveant, J.-M.,J. Am. Chem. Soc., 1987, vol. 109, p. 6788.
  10. Andrieux, C.P., Differding, E., Robert, M., and Saveant, J.-M.,J. Am. Chem. Soc., 1993, vol. 115, p. 6592.
  11. Andrieux, C.P., Le Gorande, A., and Saveant, J.-M.,J. Am. Chem. Soc., 1992, vol. 114, p. 6892.
  12. Saveant, J.-M.,Acc. Chem. Res., 1993, vol. 26, p. 455.
  13. Dessy, R.E., Kitching, W., and Chivers, T.,J. Am. Chem. Soc., 1966, vol. 88, p. 453.
  14. Hengge, E. and Firgo, H.,J. Organomet. Chem., 1981, vol. 212, p. 155.
  15. Biran, C, Bordeau, M., Pons, P.,et al., J. Organomet. Chem., 1990, vol. 382, p. 17.
  16. Kunai, A., Kawakami, T., Toyoda, E., and Ishikawa, M.,Organometallics, 1991, vol. 10, p. 893.
  17. Shono, T., Kashimura, S., Ishifune, M., and Nishida, R.,J. Chem. Soc., Chem. Commun., 1990, vol. 17, p. 1160.
  18. Corriu, R.J.P., Dabosi, G., and Martineau, M.,J. Chem. Soc., Chem. Commun., 1979, vol. 10, p. 457.
  19. Shono, T., Ohmizu, H., Kawakami, S., and Sugiyama, H.,Tetrahedron Lett., 1980, vol. 21, p. 5029.
  20. Biran, C, Bordeau, M., Bonafoux, D.,et al., J. Chem. Phys., 1996, vol. 93, p. 591.
  21. Handbook of Chemistry and Physics, Cleveland: CRC, 1994, 75th ed., p. 51.
  22. Jouikov, V.V., inCurrent Topics in Electrochemistry, 1997, vol. 4, p. 1.
  23. Zhuikov, V.V., Biran, C, Bordeau, M., and Dunogues, J.,Zh. Org. Khim., 1997, vol. 67, p. 1039.
  24. Il’yasov, A.V., Levin, Y.A., and Morozova, I.D.,J. Mol. Struct., 1973, vol. 19, p. 671.
  25. Marcus, R.A., inSpecial Topics in Electrochemistry, New York: Elsevier, 1977, p. 161.
  26. Andrieux, C.P. and Saveant, J.-M.,J. Electroanal. Chem., 1986, vol. 205, p. 43.
  27. Fleming, I.,Comprehensive Organic Chemistry, Oxford: Pergamon, 1979, vol. 3, p. 539.
  28. Mairanovskii, S.G., Ponomareko, V.A., and Barashkova, N.G.,Izv. Akad. Nauk SSSR, Ser. Khim., 1964, vol. 11, p. 1951.
  29. Mairanovskii, S.G., Ponomareko, V.A., Barashkova, N.G., and Snegova, A.D.,Dokl. Akad. Nauk SSSR, 1960, vol. 134, p. 387.
  30. Rifi, M.R.,Tetrahedron Lett., 1969, p. 1043.
  31. Andrieux, C.P., Gallardo, I., and Saveant, J.-M.,J. Am. Chem. Soc., 1989, vol. 111, p. 1620.
  32. Boberski, W.G. and Allred, A.L.,J. Org. Chem., 1975, vol. 88, p. 65.
  33. Mochida, K., Itani, A., Yokoyama, M.,et al., Kagaku to Kogyo, 1985, vol. 58, p. 2149.
  34. Fukuzumi, S., Kitano, T., and Mochida, K.,Chem. Lett., 1990, vol. 90, no. 9, p. 1741.
  35. Diaz, A., Seymour, M., Pannell, K.H., and Rozell, J.M.,J. Electrochem. Soc., 1990, vol. 137, p. 503.
  36. Zhuikov, V.V.,Zh. Org. Khim., 1997, vol. 67, p. 1037.
  37. Zhdanov, Yu.A. and. Minkin, V.I.,Korrelyatsionnyi analiz v organicheskoi khimii (The Correlation Analysis in Organic Chemistry), Rostov-on-Don: Rostov. Gos. Univ., 1966.
  38. Latypova, V.Z.,Doctoral (Chem.) Dissertation, Kazan: Kazan. State. Univ., 1985.
  39. Miller, R.D. and Michl, J.,Chem. Rev., 1989, vol. 89, p. 1359.
  40. Bock, H. and Solouki, B.,Chem. Rev., 1995, vol. 95, p. 1161.
  41. Egorochkin A.N.,Usp. Khim., 1992, vol. 61, p. 1092.
  42. Zhuikov, V.V.,Zh. Org. Khim., 1997, vol. 67, p. 1040.
  43. Becker, J.Y., Shakkour, E., and West, R.,Tetrahedron Lett., 1992, vol. 33, p. 5633.