Skip to main content
Log in

Oxidation of γ-stannyl sulfides by monochloramine CB and hydrogen peroxide

  • Organometallic Chemistry
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The first γ-trimethylstannyl sulfimide, Me3Sn(CH2)3S(=NSO2Ar)C5H11-n, was synthesized by oxidative imination of Me3Sn(CH2)3SC5H11-n with ArSO2(Na)Cl (Ar=C6H4Cl-4). Oxidation of γ-trimethylstannyl sulfimide by an alkaline solution of H2O2 gave γ-trimethylstannyl sulfoximide, Me3Sn(CH2)3S(O)(=NSO2Ar)C5H11-n, and γ-trimethylstannyl sulfone, Me3Sn(CH2)3SO2C5H11-n, the latter compound resulting from hydrolysis of the arylsulfimide group. Oxidation of stannyl sulfide by hydrogen peroxide yielded γ-trimethylstannyl sulfoxide, Me3Sn(CH2)3S(O)C5H11-n (under mild conditions) or γ-trimethylstannyl sulfone (under more severe conditions).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. V. I. Shcherbakov and N. E. Stolyarova,Metallorg. Khim., 1993,6, 330 [Organomet. Chem. USSR, 1993,6 (Engl. Transl.)].

    CAS  Google Scholar 

  2. V. I. Shcherbakov and N. E. Stolyarova,Izv. Akad. Nauk, Ser. Khim., 1994, 2024 [Russ. Chem. Bull., 1994,43, 1913 (Engl. Transl.)].

  3. T. L. Gilchrist and C. Moody,Chem. Rev., 1977,77, 409.

    Article  CAS  Google Scholar 

  4. C. R. Johnson, inComprehensive Organic Chemistry, Eds. D. Barton and W. D. Ollis,3, Pergamon Press, Oxford-New York-Toronto-Sydney-Paris-Frankfurt, 1979, 215.

    Google Scholar 

  5. I. V. Koval,Usp. Khim., 1990,59, 1409 [Russ. Chem. Rev., 1990,59 (Engl. Transl.)].

    CAS  Google Scholar 

  6. S. Oae and N. Furukawa,Sulfilimines and Related Derivatives, ACS Monograph, No. 179, Washington, 1983, 340 pp.

  7. Khimicheskii entsiklopedicheskii slovar' [Chemical Encyclopedic Dictionary], Sov. Entsiklopediya, Moscow, 1983, 551 (in Russian).

  8. Ger. Pat. 2410131, 1974;Chem. Abstrs., 1974,81, 169628u.

  9. P. J. Cox, M. S. W. Doidge-Harrison, I. W. Nowell, R. A. Howie, A. P. Randall, and J. L. Wardell,Inorg. Chim. Acta., 1990,172, 225.

    Article  CAS  Google Scholar 

  10. J. L. Wardell and J. McWigzell,J. Organomet. Chem., 1983,224, 225.

    Article  Google Scholar 

  11. J. L. Wardell and J. McWigzell,J. Organomet. Chem., 1981,205, C24.

    Article  CAS  Google Scholar 

  12. D. J. Peterson,J. Organomet. Chem., 1971,26, 215.

    Article  CAS  Google Scholar 

  13. Ger. Pat. 2231813, 1973;Chem. Abstrs., 1973,78, 84535z.

  14. Ger. Pat. 2558163, 1976;Chem. Abstr., 1976,85, 124157f.

  15. V. I. Shcherbakov and G. V. Basova, inVIIth Int. Conf. Organomet. Coord. Chem., Germanium, Tin and Lead, Abstracts, Riga, 1992, 86.

  16. V. I. Shcherbakov, I. K. Grigor'eva, N. E. Stolyarova,Tez. dokl. VI Vseros. konf. po metalloorganicheskoi khimii, [Abstract of Papers, All-Union Conf. on Organometallic Chemistry], Vol. 1, Nizhnii, Novgorod, 1995, 155 (in Russian).

    Google Scholar 

  17. C. R. Johnson, inComprehensive Organic Chemistry, Eds. D. Barton and W. D. Ollis,3, Pergamon Press, Oxford-New York-Toronto-Sydney-Paris-Frankfurt, 1979, 223.

    Google Scholar 

  18. G. C. Barrett, inComprehensive Organic Chemistry, Eds. D. Barton and W. D. Ollis,3, Pergamon Press, Oxford-New York-Toronto-Sydney-Paris-Frankfurt, 1979, 33.

    Google Scholar 

  19. R. Tsujihara, N. Furukava, and S. Oae,Bull. Chem. Soc. Jpn., 1970,43, 2153.

    Article  CAS  Google Scholar 

  20. A. J. Gordon and R. A. Ford,The Chemist's Companion. A Handbook of Practical Data, Techniques, and References, J. Wiley and Sons, New York, 1972.

    Google Scholar 

  21. V. I. Shcherbakov, V. P. Kuznetsova, E. V. Chuprunov, T. I. Ovsetsina, N. E. Stolyarova, and L. N. Zakharov,Metalloorg. Khim., 1991,4, 1350 [Organomet. Chem. USSR, 1991,4 669 (Engl. Transl.)].

    CAS  Google Scholar 

  22. W. Schoniger,Z. Anal. Chem., 1961,187, 28.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 371–374, February, 1997.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shcherbakov, V.I., Stolyarova, N.E. & Kurskii, Y.A. Oxidation of γ-stannyl sulfides by monochloramine CB and hydrogen peroxide. Russ Chem Bull 46, 358–361 (1997). https://doi.org/10.1007/BF02494381

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02494381

Key words

Navigation