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Electron transfer as the initiating stage of dehydrogenation of benzimidazolines by the triphenylmethyl cation

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

We consider a radical-ion mechanism for dehydroaromatization of benzimidazolines by triarylmethyl cations, including as the initial step electron transfer from the hydroheteroaromatic compound to the electrophilic reagent. We draw the conclusion that there is significant weakening of the C(2)-H bond in the benzimidazoline radical cation formed in this stage.

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References

  1. A. V. El'tsov and M. Z. Girshovich, Zh. Org. Khim.,3, 1332 (1967).

    Google Scholar 

  2. A. V. El'tsov, N. V. Pavlish, and V. A. Ketlinskii, Zh. Org. Khim.,14, 1751 (1978).

    Google Scholar 

  3. A. S. Morkovnik, Author's Abstract, Dissertation in competition for the academic degree of Doctor of the Chemical Sciences, Rostov-na-Donu (1991).

  4. O. Yu. Okhlobystin and N. T. Berberova, Khim. Geterotsikl. Soedin., No. 8, 1011 (1984).

  5. N. T. Berberova, E. P. Ivakhnenko, A. S. Morkovnik, and O. Yu. Okhlobystin, Khim. Geterotsikl. Soedin., No. 12, 1696 (1979).

  6. A. S. Morkovnik, E. S. Klimov, A. N. Suslov, E. P. Ivakhnenko, O. Yu, Okhlobystin, and B. A. Tertov, Khim. Geterotsikl. Soedin., No. 5, 634 (1987).

  7. A. S. Morkovnik, A. N. Suslov, and B. A. Tertov, Zh. Obhsh. Khim.,61, 471 (1991).

    Google Scholar 

  8. M. M. Baizer (ed.), Organic Electrochemistry [Russian translation], Mir, Moscow (1976).

    Google Scholar 

  9. A. S. Morkovnik, E. P. Ivakhnenko, Yu. G. Bogachev, B. A. Tertov, N. T. Berberova, and O. Yu. Okhlobystin, Khim. Geterotsikl. Soedin., No. 2, 203 (1988).

  10. H. Volz and W. Lotsch, Tetrahed. Lett., No. 27, 2275 (1969).

  11. L. Eberson and F. Radner, Acta Chem. Scand.,38B, 861 (1984).

    Google Scholar 

  12. L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer Verlag, Berlin (1987), p. 32.

    Google Scholar 

  13. A. N. Suslov, A. S. Morkovnik, and G. S. Borodkin, Teor. Éksp. Khim., No. 6, 658 (1990).

  14. L. Eberson, Adv. Phys. Org. Chem.,18, 79 (1982).

    Google Scholar 

  15. V. A. Rodionov and É. G. Rozantsev, Long-Lived Radicals [in Russian], Nauka, Moscow (1972), p. 22.

    Google Scholar 

  16. A. A. Khapicheva, N. T. Berberova, E. S. Klimov, and O. Yu. Okhlobystin, in: Abstracts, Sixth All-Union Conference on Problems of Charge-Transfer Complexes and Radical-Ion Salts [in Russian], Chernogolovks (1984), p. 180.

  17. V. E. Titov and V. G. Koshechko, in: Abstracts, Sixth All-Union Conference on Problems of Charge-Transfer Complexes and Radical-Ion Salts [in Russian], Chernogolovka (1984), p. 178.

  18. A. A. Khapicheva, N. T. Berberova, E. S. Klimov, and O. Yu. Okhlobystin, Zh. Obshch. Khim.,55, 1533 (1985).

    Google Scholar 

  19. R. W. Alder, M. Bonifacic, and K.-D. Asmus, J. Chem. Soc., Perkin Trans. 11, No. 2, 277 (1986).

  20. A. I. Shif, Dissertation in competition for the academic degree of Candidate of the Chemical Sciences, Rostov-na-Donu (1989).

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Authors
  1. A. S. Morkovnik
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  2. A. N. Suslov
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  3. E. S. Klimov
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  4. Z. S. Morkovnik
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  5. O. Yu. Okhlobystin
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Additional information

Deceased.

Scientific-Research Institute of Physical and Organic Chemistry, Rostov State University, Rostov-na-Donu 344104. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 640-643, May, 1995. Original article submitted April 20, 1995.

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Morkovnik, A.S., Suslov, A.N., Klimov, E.S. et al. Electron transfer as the initiating stage of dehydrogenation of benzimidazolines by the triphenylmethyl cation. Chem Heterocycl Compd 31, 563–566 (1995). https://doi.org/10.1007/BF01166330

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