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Reaction of p-benzoquinone with aryldiazonium salts

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Conclusions

  1. 1.

    A study was made of the effect of the hydroxyl-ion concentration, atmospheric oxygen, and the addition of hydroquinone and other reducing and oxidizing agents on the reaction of p-benzoquinone with aryldiazonium salts.

  2. 2.

    The active center, entering into reaction with the aryldiazonium salt, is the semiquinone radical, which is formed in the initial stage when an electron donor is present in the reaction medium.

  3. 3.

    A chain mechanism was proposed for the reaction of the semiquinone radical with the diazonium cation, which includes the formation of a complex and the transfer of an electron from the semiquinone to the diazonium cation with the formation of an arylsemiquinone.

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Literature cited

  1. 1.

    Organic Compounds [Russian translation], Vol. 2, Mir (1965), p. 199.

  2. 2.

    C. S. Rendestwedt and O. Vogl, J. Am. Chem. Soc.,77, 2313 (1965).

  3. 3.

    K. W. Dicherman, J. Org. Chem.,22, 1070 (1957).

  4. 4.

    J. K. Kochi, J. Am. Chem. Soc.,78, 1228 (1956).

  5. 5.

    D. E. Kvalnes, J. Am. Chem. Soc.,56, 2478 (1934).

  6. 6.

    A. A. Matnishyan, A. A. Belkin, Kh. L. Brikenshtein, B. I. Liogon'kii, and A. A. Berlin, Vysokomolekul. Soedin.,13, 1009 (1971).

  7. 7.

    C. S. Rondestvedt and O. Vogl, J. Am. Chem. Soc.,78, 3799 (1956).

  8. 8.

    G. Freund, J. Chem. Soc., 2889, 3707 (1953).

  9. 9.

    S. Carlton, I. Dicherman, and K. Weiss, J. Org. Chem.,22, 1070 (1957).

  10. 10.

    J. F. Bagli and P. L'Ecuyer, Can. J. Chem.,39, 1037 (1961).

  11. 11.

    J. Aselin, P. Brassard, and P. L'Ecuyer, Can. J. Chem.,44, 2563 (1966).

  12. 12.

    K. Schimmelschmidt, Ann. Chem.,566, 184 (1950).

  13. 13.

    German Patent 508395 (October 23, 1924); Chem. Abstr.,25, 712 (1931).

  14. 14.

    R. L. Edwards and D. Lewis, J. Chem. Soc., 3250 (1959).

  15. 15.

    J. W. Breitenbach and H. Schneider, Ber.,768, 1088 (1943).

  16. 16.

    S. A. Cohen, J. Am. Chem. Soc.,69, 1057 (1947).

  17. 17.

    P. Brassard and P. L'Ecuyer, Can. J. Chem.,36, 700, 709 (1958).

  18. 18.

    K. J. P. Orton and R. W. Everatt, J. Chem. Soc.,93, 1021 (1908).

  19. 19.

    M. Eigen and P. Matthies, Chem. Ber.,94, 3309 (1961).

  20. 20.

    G. F. Fomin, Dissertation [in Russian], Moscow (1969).

  21. 21.

    B. A. Porai-Koshits, Usp. Khim.,39, 608 (1970).

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2020–2025, September, 1972.

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Matnishyan, A.A., Prut, É.V., Fomin, G.V. et al. Reaction of p-benzoquinone with aryldiazonium salts. Russ Chem Bull 21, 1961–1965 (1972). https://doi.org/10.1007/BF00854616

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Keywords

  • Oxygen
  • Active Center
  • Electron Donor
  • Reaction Medium
  • Hydroquinone