Oxidation of γ-stannyl sulfides by monochloramine CB and hydrogen peroxide
Organometallic Chemistry
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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).
Key words
pentyl 3-(trimetylstannyl)propyl sulfide oxidation γ-trimethylstannyl sulfimide γ-trimethylstannyl sulfoximide γ-trimethylstannyl sulfoxide γ-trimethylstannyl sulfonePreview
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References
- 1.V. I. Shcherbakov and N. E. Stolyarova,Metallorg. Khim., 1993,6, 330 [Organomet. Chem. USSR, 1993,6 (Engl. Transl.)].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.)].Google Scholar
- 3.T. L. Gilchrist and C. Moody,Chem. Rev., 1977,77, 409.CrossRefGoogle 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.)].Google Scholar
- 6.S. Oae and N. Furukawa,Sulfilimines and Related Derivatives, ACS Monograph, No. 179, Washington, 1983, 340 pp.Google Scholar
- 7.Khimicheskii entsiklopedicheskii slovar' [Chemical Encyclopedic Dictionary], Sov. Entsiklopediya, Moscow, 1983, 551 (in Russian).Google Scholar
- 8.Ger. Pat. 2410131, 1974;Chem. Abstrs., 1974,81, 169628u.Google Scholar
- 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.CrossRefGoogle Scholar
- 10.J. L. Wardell and J. McWigzell,J. Organomet. Chem., 1983,224, 225.CrossRefGoogle Scholar
- 11.J. L. Wardell and J. McWigzell,J. Organomet. Chem., 1981,205, C24.CrossRefGoogle Scholar
- 12.D. J. Peterson,J. Organomet. Chem., 1971,26, 215.CrossRefGoogle Scholar
- 13.Ger. Pat. 2231813, 1973;Chem. Abstrs., 1973,78, 84535z.Google Scholar
- 14.Ger. Pat. 2558163, 1976;Chem. Abstr., 1976,85, 124157f.Google Scholar
- 15.V. I. Shcherbakov and G. V. Basova, inVIIth Int. Conf. Organomet. Coord. Chem., Germanium, Tin and Lead, Abstracts, Riga, 1992, 86.Google Scholar
- 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.CrossRefGoogle 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.)].Google Scholar
- 22.W. Schoniger,Z. Anal. Chem., 1961,187, 28.CrossRefGoogle Scholar
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