Статья
2000

Electrochemical activation of inorganic and simplest organoelement compounds in organic syntheses

N. T. Berberova N. T. Berberova
Российский электрохимический журнал
https://doi.org/10.1007/BF02756903
Abstract / Full Text
Berberova, N.T. Electrochemical activation of inorganic and simplest organoelement compounds in organic syntheses. Russ J Electrochem 36, 174–182 (2000). https://doi.org/10.1007/BF02756903

Data are presented on the reactivity of silicon and tin hydrides, phosphorus trichloride, and hydrogen sulfide in the anodic single-electron reduction of these reagents to corresponding radical cations. Organic reactions involving them are considered.

Author information

  • Astrakhan State Technical University, Astrakhan, Russia

    N. T. Berberova

References
  1. Kochi, J.K.,Organometallic Mechanisms and Catalysis: The Role of Reactive Intermediates in Organic Processes, New York: Academic, 1978, p. 48.
  2. Klingler, R.J., Mochida, A.A., and Kochi, J.K.,J. Am. Chem. Soc., 1979, vol. 101, p. 6626.
  3. The Electrochemistry of Organic Germanium, Tin, and Lead Compounds, Patai, S., Ed., Jerusalem: Wiley, 1995, pp. 278, 665, 709.
  4. Fuchigami, T.,The Chemistry of Organosilicon Compounds, Rappoport, Z., Ed., Jerusalem: Wiley, 1998, vol. 2, p. 1187.
  5. Tomilov, A.P., Chernykh, I.N., and Kargin, Yu.M.,Elektrokhimiya elementoorganicheskikh soedinenii: Elementy IV, V, VI grupp periodicheskoi sistemy (The Electrochemistry of Organometallic Compounds: Elements of Groups IV, V, and VI of the Periodic Table), Moscow: Nauka, 1986.
  6. Yochida, J., Ishichi, Y., Nishivaki, K.,et al., Tetrahedron Lett., 1992, vol. 33, p. 2599.
  7. Yochida, J., Ishichi, Y., and Isoe, S.,J. Am. Chem. Soc., 1992, vol. 114, p. 7594.
  8. Kunai, A., Kawakami, T., Toyoda, E.,et al.,Chem. Lett., 1993, p. 1945.
  9. Zhuikov, V.V.,Usp. Khim., 1997, vol. 66, p. 564.
  10. Berberova, N.T. and Okhlobystin, O.Yu.,Dokl. Ross. Akad. Nauk, 1993, vol. 332, p. 560.
  11. Klimov, E.S., Bumber, A.A., and Okhlobystin, O.Yu.,Zh. Obshch. Khim., 1983, vol. 53, p. 1739.
  12. Mann, Ch.K. and Barnes, K.K.,Electrochemical Reactions in Nonaqueous Systems, New York: Marcel Dekker, 1970.
  13. McKinley, A.J., Claridge, R.F.C., and Harland, P.W.,J. Chem. Phys., 1986, vol. 102, p. 283.
  14. Murthy, K. and Blat, S.V.,Chem. Phys. Lett., 1987, vol. 133, p. 455.
  15. Grinberg, V.A., Kokh, E.A., Mazin, V.M.,et al.,Izv. Ross. Akad. Nauk: Ser. Khim., 1999, p. 295.
  16. Weissberger, A., Proskauer, E.S., Riddick, J.A., and Toops, E.E.,Organic Solvents: Physical Properties and Methods of Purification, New York: Interscience, 1955.
  17. Andrianov, K.A.,Metody elementoorganicheskoi khimii: Kremnii (Methods of the Organoelement Chemistry: Silicon), Moscow: Nauka, 1968.
  18. Andrianov, K.A.,Metody elementoorganicheskoi khimii: Olovo (Methods of the Organoelement Chemistry: Tin), Moscow: Nauka, 1968.
  19. Baudler, M., Brauer, G., Feher, F.,et al., Handbuch der Praeparativen anorganischen Chemie, in 4 vols., Brauer, G., Ed., Stuttgart: Ferdinand Enke, 1975–1981.
  20. Berberova, N.T. and Okhlobystin, O.Yu.,Zh. Obshch. Khim., 1981, vol. 51, p. 224.
  21. Stradins, J.P.,Polyarografiya v organicheskoi khimii (Polarography in Organic Chemistry), Leningrad: Khimiya, 1974, p. 102.
  22. Berberova, N.T.,Doctoral (Chem.) Dissertation, Rostov: Rostov. State Univ., 1991.
  23. Albery, W.J. and Bruckenstain, S.,Trans. Faraday Soc., 1966, vol. 62, p. 1946.
  24. Khapicheva, A.A., Klimov, E.S., Berberova, N.T., and Okhlobystin, O.Yu., Abstracts of Papers,IV Vsesoyuz. soveshch. “ Kompleksy s perenosom zaryada i ionradikal’nye soli ” (IV All-Union Meeting on the Charge Transfer Complexes and Radical-Ion Salts), Chernogolovka, 1984, p. 180.
  25. Khapicheva, A.A., Berberova, N.T., and Okhlobystin, O.Yu.,Kinetika radikal’nykh reaktsii v zhidkoi faze (Kinetics of Radical Reactions in a Liquid Phase), Gor’kii, 1987, p. 57.
  26. Ojima, J. and Kumagai, M.,J. Org. Chem., 1976, vol. 111, p. 43.
  27. Neuman, W.P.,The Organic Chemistry of Tin, Stuttgart, 1967.
  28. Lopatina, VS., Kochetkov, K.A., Fomina, N.V.,et al., Zh. Obshch. Khim., 1981, vol. 51, p. 2570.
  29. Franko, G.J., Resnic, R., and Dillara, C.R.,J. Org. Chem., 1985, vol. 4, p. 57.
  30. Berberova, N.T., Khapicheva, A.A., Mishenina, I.V.,et al., Zh. Sev.-Kavk. Nauch. Tsentra Vyssh. Shkoly, 1991, vol. 2, p. 81.
  31. Berberova, N.T., Khapicheva, A.A., Mishenina, I.V.,et al., Abstracts of Papers,VII Vsesoyuz. konf. po elektrokhimii (VII All-Union Conf. on Electrochemistry), Chernovtsy, 1988, vol. 3, p. 160.
  32. Khapicheva, A.A., Berberova, N.T., and Okhlobystin, O.Yu., Abstracts of Papers,VII Vsesoyuz. soveshch. “ Kompleksy s perenosom zaryada i ion-radikal’nye soli ” (VII All-Union Meet. on the Charge Transfer Complexes and Radical-Ion Salts), Chernogolovka, 1988, p. 214.
  33. Berberova, N.T., Khapicheva, A.A., and Barakaeva, L.R., Abstracts of Papers,XIV Mendeleevskii s“ezd po obshchei i prikladnoi khimii (XIV Mendeleev Congress on General and Applied Chemistry), Tashkent, 1989, vol. l, p. 51.
  34. Hudson, R.,Structure and Mechanism in Organophosphorus Chemistry, London, 1965.
  35. Tsvetkov, E.N. and Kabachnik, M.I.,Reaktsii i metody issledovaniya organicheskikh soedinenii (Reactions and Investigation Techniques of Organic Compounds), Moscow: Khimiya, 1964, vol. 13, p. 267.
  36. Rakhimov, A.I.,Sintez fosfororganicheskikh soedinenii (Synthesis of Organophosphorus Compounds), Moscow: Nauka, 1985.
  37. Shiavon, G., Zecchin, S., and Cogoni, G.,J. Electroanal. Chem., 1973, vol. 48, p. 425.
  38. Cara, W.B. and Roberts, B.P.,J. Chem. Soc., Perkin Trans., 1978, no. 6, p. 150.
  39. Klimov, E.S., Vakar, A.A., Sokolov, V.I., and Okhlobystin, O.Yu.,Zh. Obshch. Khim., 1987, vol. 57, p. 831.
  40. Sogomonova, A.G., Berberova, N.T., Kazarov, A.A., and Okhlobystin, O.Yu.,Elektrokhimiya, 1984, vol. 20, p. 1326.
  41. Kargin, Yu.M., Nikitin, E.V., and Romanov, L.V.,Dokl. Akad. Nauk SSSR, 1976, vol. 226, p. 1101.
  42. Flurry, R.L. and Boozes, S.E.,J. Org. Chem., 1960, vol. 31, p. 2078.
  43. Nekhoroshev, M.V., Panov, V.B., Bumber, A.A., and Okhlobystin, O.Yu.,Zh. Obshch. Khim., 1980, vol. 50, p. 958.
  44. Berberova, N.T., Dorofeenko, G.N., and Okhlobystin, O.Yu.,Khim. Geterotsikl. Soed., 1977, no. 3, p. 318.
  45. Berberova, N.T. and Okhlobystin, O.Yu.,Zh. Obshch. Khim., 1996, vol. 66, p. 1796.
  46. Deryagina, E.N., Abstracts of Papers,18 konf. po khimii i tekhnologii organicheskikh soedinenii sery (18th Conf. on the Chemistry and Technology of Organic Compounds of Sulfur), Kazan, 1992, p. 60.
  47. Gronowitz, E.S.,Thiopene and Its Derivatives, New York: Interscience, 1985, p. 24.
  48. Ryashentseva, M.A.,Usp. Khim., 1994, vol. 63, p. 456.
  49. Papernaya, L.K., Panova, G.N., Deryagina, E.N., and Voronkov, M.G.,Zh. Org. Khim., 1993, vol. 29, p. 2241.
  50. Budanov, V.V. and Makarov, S.V.,Khimiya serosoderzhashchikh vosstanovitelei (The Chemistry of Sulfur-Containing Reducing Agents), Moscow: Khimiya, 1994.
  51. Murav’ev, O.N., Makarov, S.V., Bazanov, M.I., and Budanov, V.V.,Zh. Obshch. Khim., 1996, vol. 66, p. 1416.
  52. Esida, K.,Elektrookislenie v organicheskoi khimii (Electrochemical Oxidation Processes in Organic Chemistry), Moscow: Mir, 1987, p. 35.
  53. Cottrel, P.T. and Mann, C.K.,J. Electrochem. Soc., 1969, vol. 36, p. 1499.
  54. Kargin, Yu.M., Latypova, V.Z., and Yakovleva, O.G., Abstracts of Papers,X Vsesoyuz. soveshch. po elektrokhimii organicheskikh soedinenii (X All-Union Conf. on the Electrochemistry of Organic Compounds), Novocherkassk: Novocherkasskii Politekh. Inst., 1980, p. 176.
  55. Latypova, V.Z., Zhuikov, V.V., and Chmutova, G.A.,Zh. Obshch. Khim., 1984, vol. 54, p. 1551.
  56. Latypova, V.Z., Yakovleva, O.G., and Zhuikov, V.V.,Zh. Obshch. Khim., 1984, vol. 54, p. 1085.
  57. Letichevskaya, N.N., Shinkar’, E.V., Berberova, N.T., and Okhlobystin, O.Yu.,Zh. Obshch. Khim., 1996, vol. 66, p. 1785.
  58. Berberova, N.T., Shinkar, E.V., Generalova, A.G., and Fomenko, A.I., Abstracts of Papers,Int. Symp. “ Organometallic Chemistry on the Eve of the 21st Century, ” Moscow, 1998, p. 20.
  59. Shinkar’, E.V., Letichevskaya, N.N., Berberova, N.T., and Okhlobystin, O.Yu.,Astrakhan. Vestnik, Moscow, 1995, p. 15.
  60. Berberova, N.T., Letichevskaya, N.N., and Shinkar’, E.V., Abstracts of Papers,XVI Mendeleevskii sezd po obshchei i prikladnoi khimii (XVI Mendeleev Congress on General and Applied Chemistry), Moscow, 1998, vol. 1, p. 46.
  61. Shinkar’, E.V.,Cand. Sci. (Chem.) Dissertation, Saratov: Saratov. State Univ., 1998.