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Electroreduction of benzo-1,2,3-dithiazolium salts and their selenium analogs in nonaqueous solution

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The electroreduction of benzo-1,2,3-dithiazolium cations and their selenium analogs in aprotic solvents takes place in two steps. The first step is a reversible, one-electron transfer leading to the formation of stable radicals detected by EPR. As a result of further electroreduction, the radicals obtained combine with six electrons to form the corresponding o-aminothio(seleno)phenols. Analysis of the reduction potentials of the compounds studied shows that the substitution of a selenium atom for a sulfur in these cations, especially in the 2 position of the heterocycle, facilitates their electrochemical reduction. The electrochemical activity and the kinetics of nulceophilic substitution in the cations studied are compared.

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Literature cited

  1. A. M. Evdokimov, Yu. I. Akulin, B. Kh. Strelets, and L. S. Efros, Khim. Geterotsikl. Soedin., 1975, No. 10, 1429.

    Google Scholar 

  2. Yu. I. Akulin, B. Kh. Strelets, and L. S. Efros, Khim. Geterotsikl. Soedin., 1975, No. 2, 275.

    Google Scholar 

  3. Yu. I. Akulin, B. Kh. Strelets, and L. S. Efros, Khim. Geterotsikl. Soedin., 1974, No. 1, 138.

    Google Scholar 

  4. B. Kh. Strelets, L. S. Afros, and V. Z. Todres, Khim. Geterotsikl. Soedin., 1970, No. 3, 351.

    Google Scholar 

  5. B. Kh. Strelets, M. M. Gel'mont, Yu. I. Akulin, and L. S. Efros, Khim. Geterotsikl. Soedin., 1978, No. 7, 912.

    Google Scholar 

  6. B. Kh. Strelets, M. M. Gel'mont, Yu. I. Akulin, and L. S. Efros, Khim. Geterotsikl. Soedin., 1979. No. 9, 912.

    Google Scholar 

  7. Yu. I. Akulin, Dissertation for the Degree Candidate in Chemical Sciences, Textile Institute, Leningrad (1975).

    Google Scholar 

  8. V. Sh. Tsveniashvili, Summary Reports of the Vllth AH-Union Conference on Polarography [in Russian], Tbilisi (1978), p. 38.

  9. V. Sh. Tsveniashvili, in: Contemporary Aspects of Electrochemical Kinetics [in Russian], Metsniereba, Tbilisi (1980), p. 138.

    Google Scholar 

  10. V. Sh. Tsveniashvili, Elektrokhimiya, 36, 751 (1980).

    Google Scholar 

  11. V. Sh. Tsveniashvili, Z. V. Todres, and S. I. Zhdanov, Zh. Obshch. Khim., 38, 1888 (1968).

    Google Scholar 

  12. V. Sh. Tsveniashvili, B. Kh. Strelets, M. V. Malashkhiya, G. I. Eremeeva, and V. N. Gaprindashvili, Izv. Akad. Nauk Gruz. SSR, Ser. Khim., 1979, No. 3, 280.

    Google Scholar 

  13. V. Sh. Tsveniasvili, M. V. Malashkhiya, B. Kh. Strelets, G. I. Eremeeva, and V. N. Gaprindashvili, Izv. Akad. Nauk Gruz. SSR, Ser. Khim., 1980, No. 1, 60.

    Google Scholar 

  14. A. Alred, J. Inorg. Nucl. Chem., 17, 215 (1961).

    Google Scholar 

  15. J. F. Coetzee, G. P. Cunningham, D. K. McGuire, and G. R. Padmanabham, Anal. Chem., 34, 1139 (1962).

    Google Scholar 

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Authors and Affiliations

  1. Institute of Inorganic Chemistry and Electrochemistry, Academy of Sciences of the Georgian SSR, 380093, Tbilisi

    V. Sh. Tsveniashvili, M. V. Malashkhiya, V. N. Gaprindashvili, B. Kh. Strelets, M. M. Gel'mont & Yu. I. Akulin

  2. Leningrad Branch with Pilot Plant of the All-Union Scientific-Research and Planning Institute of Synthetic Fibers, 195030, Leningrad

    V. Sh. Tsveniashvili, M. V. Malashkhiya, V. N. Gaprindashvili, B. Kh. Strelets, M. M. Gel'mont & Yu. I. Akulin

Authors
  1. V. Sh. Tsveniashvili
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  2. M. V. Malashkhiya
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  3. V. N. Gaprindashvili
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  4. B. Kh. Strelets
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  5. M. M. Gel'mont
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  6. Yu. I. Akulin
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 219–222, February, 1985.

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Tsveniashvili, V.S., Malashkhiya, M.V., Gaprindashvili, V.N. et al. Electroreduction of benzo-1,2,3-dithiazolium salts and their selenium analogs in nonaqueous solution. Chem Heterocycl Compd 21, 181–184 (1985). https://doi.org/10.1007/BF00504205

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  • DOI: https://doi.org/10.1007/BF00504205

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