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Chlorine dioxide in chemo- and stereoselective oxidation of sulfides

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Abstract

Data on oxidation of alkyl-, phenyl-, benzyl-, oxo-, and terpenyl-substituted and nitrogen-containing heterocyclic sulfides with chlorine dioxide are reviewed. The oxidation is highly chemoselective and moderately stereo- and enantioselective.

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References

  1. E. Wojaczysska, J. Wojaczysski, Chem. Rev., 2010, 110, 4303.

    Article  Google Scholar 

  2. I. Fernández, N. Khiar, Chem. Rev., 2003, 103, 3651.

    Article  Google Scholar 

  3. G. Hanquet, F. Colobert, S. Lanners, G. Solladié, ARKIVOC, 2003, 7, 328.

    Article  Google Scholar 

  4. P. Kowalski, K. Mitka, K. Ossowska, Z. Kolarska, Tetrahedron, 2005, 61, 1933.

    Article  CAS  Google Scholar 

  5. W. J. Masschelein, Chlorine Dioxide: Chemistry and Enviromental Impact of Oxychlorine Compounds, Ann Arbor Publ., Inc., Ann Arbor, 1979, 418 pp.

    Google Scholar 

  6. C. Rav-Acha, E. Choshen, S. Sarel, Helv. Chim. Acta, 1986, 69, 1728.

    Article  CAS  Google Scholar 

  7. G. Gordon, R. G. Kieffer, D. H. Rosenblatt, The Chemistry of Chlorine Dioxide, Wiley Interscience Publ., New York-London-Sydney-Toronto, 1972, 348 pp.

    Google Scholar 

  8. S. V. Sharma, React. Kinet. Catal. Lett., 1982, 19, 167.

    Article  CAS  Google Scholar 

  9. S. V. Sharma, Rev. Roum. Chim., 1983, 28, 967.

    CAS  Google Scholar 

  10. A. V. Kutchin, L. L. Frolova, I. V. Dreval’, Russ. Chem. Bull. (Engl. Transl.), 1996, 45, 1781 [Izv. Akad. Nauk, Ser. Khim., 1996, 1871].

    Article  Google Scholar 

  11. L. L. Frolova, A. V. Popov, S. A. Rubtsova, A. V. Kutchin, Khim. Prir. Soedin., 2008, 585 [Chem. Nat. Compd. (Engl. Transl.), 2008, 44, 724].

    Google Scholar 

  12. E. S. Ganieva, I. M. Ganiev, S. A. Grabovskii, N. N. Kabal’nova, Russ. Chem. Bull. (Int. Ed.), 2008, 57, 2328 [Izv. Akad. Nauk, Ser. Khim., 2008, 2283].

    Article  CAS  Google Scholar 

  13. J. Otto, K. Paluch, Roczniki Chem., 1965, 39, 1711.

    CAS  Google Scholar 

  14. E. S. Ganieva, I. M. Ganiev, S. A. Grabovskii, N. N. Kabal’nova, Russ. Chem. Bull. (Int. Ed.), 2008, 57, 2332 [Izv. Akad. Nauk, Ser. Khim., 2008, 2287].

    Article  CAS  Google Scholar 

  15. E. Grimley, G. Gordon, J. Inorg. Nucl. Chem., 1973, 35, 2383.

    Article  CAS  Google Scholar 

  16. D. H. Rosenblatt, L. A. Hull, D. C. De Luca, G. T. Davis, R. C. Weglein, H. K. R. Williams, J. Am. Chem. Soc., 1967, 89, 1158.

    Article  CAS  Google Scholar 

  17. I. V. Loginova, I. Yu. Chukicheva, A. V. Kutchin, Zh. Org. Khim., 2011, 47, 1475 [Russ. J. Org. Chem. (Engl. Transl.), 2011, 47, 1501].

    Google Scholar 

  18. L. A. Hull, G. T. Davis, D. H. Rosenblatt, H. K. R. Williams, R. C. Weglein, J. Am. Chem. Soc., 1967, 89, 1163.

    Article  CAS  Google Scholar 

  19. G. T. Davis, M. M. Demek, D. H. Rosenblatt, J. Am. Chem. Soc., 1972, 94, 3321.

    Article  CAS  Google Scholar 

  20. RF Pat. 2127258; Byull. Izobret. [Bulletin of Inventions], 1999, No. 7 (in Russian).

  21. RF Pat. 2139275; Byull. Izobret. [Bulletin of Inventions], 1999, No. 28 (in Russian).

  22. RF Pat. 2440336; Byull. Izobret. [Bulletin of Inventions], 2012, No. 2 (in Russian).

  23. A. V. Kutchin, S. A. Rubtsova, L. P. Karmanova, S. N. Subbotina, I. V. Loginova, Russ. Chem. Bull. (Engl. Transl.), 1998, 47, 2051 [Izv. Akad. Nauk, Ser. Khim., 1998, 2110].

    Article  Google Scholar 

  24. A. V. Kutchin, S. A. Rubtsova, I. V. Loginova, S. N. Subbotina, Zh. Org. Khim., 2000, 36, 1873 [Russ. J. Org. Chem. (Engl. Transl.), 2000, 36, 1819].

    Google Scholar 

  25. A. V. Kutchin, S. A. Rubtsova, I. V. Loginova, Russ. Chem. Bull. (Int. Ed.), 2001, 50, 432 [Izv. Akad. Nauk, Ser. Khim., 2001, 413].

    Article  CAS  Google Scholar 

  26. D. V. Sudarikov, S. A. Rubtsova, A. V. Kutchin, Mendeleev Commun., 2008, 18, 225.

    Article  CAS  Google Scholar 

  27. D. V. Sudarikov, V. A. Kuropatov, S. A. Rubtsova, V. K. Cherkasov, A. V. Kutchin, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. [Bulletin of High Schools, Chemistry and Chemical Technology], 2008, 51, 112 (in Russian).

    CAS  Google Scholar 

  28. I. V. Loginova, E. V. Ashikhmina, S. A. Rubtsova, Yu. V. Krymskaya, A. V. Kutchin, Zh. Org. Khim., 2008, 44, 1799 [Russ. J. Org. Chem. (Engl. Transl.), 2008, 44, 1773].

    Google Scholar 

  29. I. V. Loginova, K. S. Rodygin, S. A. Rubtsova, P. A. Slepukhin, A. V. Kutchin, V. A. Polukeev, Zh. Org. Khim., 2011, 47, 125 [Russ. J. Org. Chem. (Engl. Transl.), 2011, 47, 124].

    Google Scholar 

  30. K. S. Rodygin, S. A. Rubtsova, A. V. Kutchin, Zh. Org. Khim., 2011, 47, 1407 [Russ. J. Org. Chem. (Engl. Transl.), 2011, 47, 1433].

    Google Scholar 

  31. Yu. V. Krymskaya, I. V. Loginova, S. A. Rubtsova, A. V. Kutchin, Zh. Org. Khim., 2013, 49, 215 [Russ. J. Org. Chem. (Engl. Transl.), 2013, 49, 204].

    Google Scholar 

  32. A. V. Kutchin, E. V. Ashikhmina, S. A. Rubtsova, I. A. Dvornikova, Khimiya rastitel’nogo syr’ya [Chemistry of Plant Raw Materials], 2009, No. 1, 59 (in Russian).

    Google Scholar 

  33. E. V. Ashikhmina, S. A. Rubtsova, I. A. Dvornikova, A. V. Kutchin, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. [Bulletin of High Schools, Chemistry and Chemical Technology], 2008, 51, 45 (in Russian).

    CAS  Google Scholar 

  34. E. V. Ashikhmina, S. A. Rubtsova, I. A. Dvornikova, A. V. Kutchin, Zh. Org. Khim., 2009, 45, 1525 [Russ. J. Org. Chem. (Engl. Transl.), 2009, 45, 1509].

    Google Scholar 

  35. I. A. Dvornikova, L. L. Frolova, A. V. Churakov, A. V. Kutchin, Russ. Chem. Bull. (Int. Ed.), 2004, 53, 1323 [Izv. Akad. Nauk, Ser. Khim., 2004, 1270].

    Article  CAS  Google Scholar 

  36. K. S. Rodygin, S. A. Rubtsova, A. V. Kutchin, I. V. Loginova, V. A. Polukeev, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. [Bulletin of High Schools, Chemistry and Chemical Technology], 2010, 53, 16 (in Russian).

    CAS  Google Scholar 

  37. K. S. Rodygin, Yu. V. Krymskaya, S. A. Rubtsova, A. V. Kutchin, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. [Bulletin of High Schools, Chemistry and Chemical Technology], 2011, 54, 21 (in Russian).

    CAS  Google Scholar 

  38. M. Ya. Demakova, D. V. Sudarikov, S. A. Rubtsova, I. V. Gruzdev, A. V. Kutchin, Zh. Org. Khim., 2012, 48, 1510 [Russ. J. Org. Chem. (Engl. Transl.), 2012, 48, 1490].

    Google Scholar 

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Authors and Affiliations

  1. Institute of Chemistry, Komi Research Center, Ural Branch of the Russian Academy of Sciences, 48 ul. Pervomaiskaya, 167982, Syktyvkar, Russian Federation

    A. V. Kutchin, S. A. Rubtsova, D. V. Sudarikov & M. Ya. Demakova

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  1. A. V. Kutchin
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  2. S. A. Rubtsova
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  3. D. V. Sudarikov
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  4. M. Ya. Demakova
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Corresponding author

Correspondence to S. A. Rubtsova.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0001–0005, January, 2013.

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Kutchin, A.V., Rubtsova, S.A., Sudarikov, D.V. et al. Chlorine dioxide in chemo- and stereoselective oxidation of sulfides. Russ Chem Bull 62, 1–5 (2013). https://doi.org/10.1007/s11172-013-0001-9

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  • DOI: https://doi.org/10.1007/s11172-013-0001-9

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