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Electrochemical amination of unsaturated and aromatic compounds

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Abstract

The mechanism and synthetic perspectives of an indirect cathodic amination of unsaturated and aromatic substrates are considered. The influence of experimental conditions on the state and reactivity of the aminating reagent in solution is studied. The key role of the electrolyte acidity and redox properties of the reagents and intermediates in the obtained isomeric composition and the yield of the amination products is demonstrated.

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References

  1. Kargin, Yu.M., Chichirov, A.A., Ustyugov, A.N., and Khusaenov, N.M.,Elektrokhimiya, 1992, vol. 29, p. 165.

    Google Scholar 

  2. Budnikova, Y. and Kargin, Y.,J. Organomet. Chem., 1997, vol. 536-537, p. 265.

    Article  Google Scholar 

  3. Budnikova, Y.H., Kargin, Y.M., and Sinyashin, O.G., Abstracts of Papers,XIV Int. Conf. on Phosphorus Chemistry, Cincinnati, Ohio, 1998, p. 3.

  4. Feroci, G. and Lund, H.,Acta Chem. Scand., 1976, vol. 30, p. 651.

    Article  Google Scholar 

  5. Davis, P., Evans, M.G., and Higginson, W.C.E.,J. Chem. Soc., 1951, p. 2563.

  6. Obshchaya organicheskaya khimiya (The General Organic Chemistry), Kochetkov, N.K. and Bakinovskii, L.V., Eds., Moscow: Khimiya, 1982, vol. 3.

    Google Scholar 

  7. Citterio, A., Gentile, A., and Minisci, F.,J. Org. Chem., 1984, vol. 49, p. 4479.

    Article  CAS  Google Scholar 

  8. Tomat, R. and Rigo, A.,J. Electroanal. Chem., 1972, vol. 35, p. 21.

    Article  CAS  Google Scholar 

  9. Tomat, R. and Rigo, A.,J. Electroanal. Chem., 1974, vol. 50, p. 345.

    Article  CAS  Google Scholar 

  10. Koutecky, J.,Collect. Czech. Chem. Commun., 1953, vol. 18, p. 311.

    CAS  Google Scholar 

  11. Galus, Z.,Teoreticzne Podstawy Electroanalizu Chemiczne, Warsaw: Panstw. Wyd. Naukowe, 1971.

    Google Scholar 

  12. Saveant, J.M. and Vianello, E.,Electrochim. Acta, 1965, vol. 10, p. 905.

    Article  CAS  Google Scholar 

  13. Farnia, G., Anselmi, D., and Vianello, E.,Ric. Sci., 1968, vol. 38, p. 1211.

    CAS  Google Scholar 

  14. Kelusharu, A.,Usp. Khim., 1979, vol. 48, p. 221.

    Google Scholar 

  15. Lisitsyn, Yu.A.,Cand. Sci. (Chem.) Dissertation, Kazan: Kazan. State Univ., 1991.

    Google Scholar 

  16. Koryta, I.,Collect. Czech. Chem. Commun., 1954, vol. 19, p. 666.

    Google Scholar 

  17. Tomat, R. and Rigo, A.,J. Electroanal. Chem., 1975, vol. 59, p. 191.

    Article  CAS  Google Scholar 

  18. Kvaratskheliya, R.K.,Elektrokhimiya gidroksilamina (The Electrochemistry of Hydroxylamine), Tbilisi: Metsniereba, 1981.

    Google Scholar 

  19. Briegleb, G.,Z. Electrochem., 1949, p. 350.

  20. Lisitsyn, Yu.A. and Kargin, Yu.M.,Zh. Obshch. Khim., 1993, vol. 63, p. 2542.

    CAS  Google Scholar 

  21. Tomat, R. and Rigo, A.,J. Inorg. Nucl. Chem., 1974, vol. 36, p. 611.

    Article  CAS  Google Scholar 

  22. Varlamov, V.T., Denisov, N.N., Nadtochenko, V.A., and Marchenko, E.P.,Kinet. Ratal, 1994, vol. 35, p. 833.

    CAS  Google Scholar 

  23. Neta, P., Maruthamuthu, P., Carton, P.M., and Fessenden, R.W.,J. Phys. Chem., 1978, vol. 82, p. 1875.

    Article  CAS  Google Scholar 

  24. Michejda, Ch.J. and Campbell, D.H.,Tetrahedron Lett., 1977, p. 577.

  25. Minisci, F.,Synthesis, 1973, no. 1, p. 1.

  26. Minisci, F.,Proc. NATO Adv. Res. Workshop, Louvain-la Neuve, 1986, p. 391.

  27. Tarrago,X., Ann. Chim., 1960, no. 1, p. 5.

  28. Simic, M. and Hayon, E.,J. Am. Chem. Soc., 1971, vol. 93, p. 5982.

    Article  CAS  Google Scholar 

  29. Fessenden, R.W. and Neta, P.,J. Phys. Chem., 1972, vol. 76, p. 2857.

    Article  CAS  Google Scholar 

  30. Yip, R.W., Vidoczy, T., Snyder, R.W., and Chow, Y.L.,J. Phys. Chem., 1978, vol. 82, p. 1194.

    Article  CAS  Google Scholar 

  31. Gilbert, B.C. and Marriott, P.R.,J. Chem. Soc., Perkin Trans. 2, 1977, p. 987.

    Google Scholar 

  32. Farnia, G., Tomat, R., and Vianello, E.,J. Chem. Soc., Perkin Trans. 2, 1975, p. 763.

    Google Scholar 

  33. Farnia, G., Sansona, G., and Vianello, E.,J. Electroanal. Chem., 1980, vol. 108, p. 245.

    Article  CAS  Google Scholar 

  34. Malatesta, V. and Ingold, K.U.,J. Am. Chem. Sci., 1973, vol. 95, p. 6400.

    Article  CAS  Google Scholar 

  35. Farnia, G., Sansona, G., and Vianello, E.,J. Electroanal. Chem., 1978, vol. 88, p. 147.

    Article  CAS  Google Scholar 

  36. Albisetti, C.J., Coffman, D.D., Hoover, F.W.,et al., J. Am. Chem. Sci., 1959, vol. 81, p. 1489.

    Article  CAS  Google Scholar 

  37. Lisitsyn, Yu.A. and Kargin, Yu.M.,Zh. Obshch. Khim., 1993, vol. 63, p. 1312.

    CAS  Google Scholar 

  38. Smirnov, Yu.D., Fedorova, L.A., and Tomilov, A.P.,Elektrokhimiya, 1992, vol. 28, p. 588.

    CAS  Google Scholar 

  39. Chiba, T. and Takata, Y,Bull. Chem. Soc. Jpn., 1978, vol. 51, p. 1418.

    Article  CAS  Google Scholar 

  40. Lisitsyn, Yu.A., Belyaeva, L.V., Sinyashin, O.G., and Kargin, Yu.M.,Zh. Obshch. Khim., 1999, vol. 69, p. 1196.

    Google Scholar 

  41. Cook, R.L. and Sammells, A.F.,J. Electrochem. Sci., 1989, vol. 136, p. 1845.

    Article  CAS  Google Scholar 

  42. Tomat, R. and Rigo, A.,J. Electroanal. Chem., 1977, vol. 75, p. 629.

    CAS  Google Scholar 

  43. Steckhan, E.,Habilitationsschrift, Muenster, Westfalischen Univ., 1977.

    Google Scholar 

  44. Mel’nikov, B.V., Lisitsyn, Yu.A., and Kargin, Yu.M.,Zh. Obshch. Khim., 1992, vol. 62, p. 2745.

    CAS  Google Scholar 

  45. Lisitsyn, Yu.A. and Kargin, Yu.M.,7th IUPAC Symp. on Organometallic Chemistry Directed towards Organic Synthesis, Kobe (Japan), 1993, p. 119.

  46. Lisitsyn, Yu.A. and Kargin, Yu.M., Abstracts of Papers,2nd Int. Symp. on Electroorganic Synthesis, Kurashiki (Japan), 1994, p. 223.

  47. Lisitsyn, Yu.A., Kononchuk, A.M., and Kargin, Yu.M.,Zh. Obshch. Khim., 1996, vol. 66, p. 2034.

    CAS  Google Scholar 

  48. Lisitsyn, Yu.A., Kononchuk, A.M., and Kargin, Yu.M.,Zh. Obshch. Khim., 1997, vol. 67, p. 646.

    Google Scholar 

  49. Lisitsyn, Yu.A. and Kargin, Yu.M.,Zh. Obshch. Khim., 1994, vol. 64, p. 1758.

    CAS  Google Scholar 

  50. Lisitsyn, Yu.A. and Kargin, Yu.M.,Zh. Obshch. Khim., 1995, vol. 65, p. 2020.

    CAS  Google Scholar 

  51. Lisitsyn, Yu.A. and Kargin, Yu.M.,Zh. Obshch. Khim., 1996, vol. 66, p. 168.

    CAS  Google Scholar 

  52. Lisitsyn, Yu.A. and Kargin, Yu.M.,191st Meet. of the Electrochemical Society, Montreal, Canada, 1997, vol. 97-1, p. 1255.

    Google Scholar 

  53. Lisitsyn, Yu. and Kargin, Yu.,9th IUPAC Symp. on Organometallic Chemistry Directed towards Organic Synthesis, Goettingen (Germany), 1997, p. 248.

  54. Lisitsyn, Yu.A. and Kargin, Yu.M.,Zh. Obshch. Khim., 1994, vol. 64, p. 1757.

    CAS  Google Scholar 

  55. Lisitsyn, Yu.A., Makarova, O.N., and Kargin, Yu.M.,Zh. Obshch. Khim., 1999, vol. 69, p. 286.

    Google Scholar 

  56. Lisitsyn, Yu.A., Makarova, O.N., and Kargin, Yu.M.,Zh. Obshch. Khim., 1999, vol. 69, p. 864.

    Google Scholar 

  57. Hartshorn, S.R. and Ridd, J.H.,J. Chem. Soc. (B), 1968, p. 1063.

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  1. Kazan State University, ul. Lenina 18, Kazan, 420008, Tatarstan, Russia

    Yu. A. Lisitsyn & Yu. M. Kargin

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  1. Yu. A. Lisitsyn
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Lisitsyn, Y.A., Kargin, Y.M. Electrochemical amination of unsaturated and aromatic compounds. Russ J Electrochem 36, 89–99 (2000). https://doi.org/10.1007/BF02756893

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  • DOI: https://doi.org/10.1007/BF02756893

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