Abstract
The initial formation of organotin derivatives with Sn-S-N bonds in heterolytic reactions of hexamethylditin or trimethyltin sulfide withN-(chlorothio)phthalimide is suggested. Subsequent interaction of these compounds with sulfenyl chloride affordsN, N′-thioorN, N′-dithiobisphthalimide. Homolytic reaction of hexamethylditin withN, N′-dithiobisphthalimide also occursvia an organotin intermediate, which, in the absence of a nucleophilic reagent, eliminates sulfur and converts intoN-trimethylstannylphthalimide.
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References
N. E. Stolyarova, Ph. D. (Chem.) Thesis, Gor'kii, 1984 (in Russian).
V. I. Shcherbakov, E. F. Ivanov, S. Ya. Khorshev, M. S. Feldman, E. B. Kopytov, and T. N. Konkina,Synth. React. Inorg. Met.-Org. Chem., 1991,21, 1549.
V. I. Shcherbakov, M. S. Fel'dman, E. B. Kopytov, and E. F. Ivanov,IV Vsesoyuz. konf. po biopovrezhdeniyam. Tezdokl. [IV-th All-Union Conference on Biological Damages, Abstrs.], Nizhnii Novgorod, 1991, 82 (in Russian).
V. I. Shcherbakov, N. E. Stolyarova, V. P. Kuznetsova, V. V. Simonov, and L. L. Frolkova,Metalloorg. Khim., 1992,5, 632 [Organomet. Chem., 1992,5 (Engl. Transl.)].
I. K. Grigor'eva, Ph. D. (Chem.) Thesis, Gor'kii, 1988 (in Russian).
M. Behforouz and J. E. Kerwood,J. Org. Chem., 1969,34, 51.
V. D. Il'ichev, B. V. Bocharov, and M. V. Gorlenko,Ekologicheskie osnovy zashchity ot biopovrezhdenii [Ecologictal Fundamentals of Protection from Biological Damages], Nauka, Moscow, 1985 (in Russian).
Yu. G. Gololobov and N. I. Gusar',Sul'fenilkhloridy [Sulfenyl Chlorides], Nauka, Moscow, 1989 (in Russian).
D. R. Hogg, inComprehensive Organic Chemistry, vol. 3, Eds. D. Barton and W. D. Ollis, Pergamon Press, Oxford, 1979, 261.
O. S. D'yachkovskaya and V. I. Shcherbakov, inMetalloorganicheskie soedineniya i radikaly [Organometallic Compounds and Radicals], Ed. M. I. Kabachnik, Nauka, Moscow, 1985, 218 (in Russian).
D. H. Harpp and T. G. Back,Tetrahedron Lett, 1972, 1481.
D. R. Hogg, inComprehensive Organic Chemistry, vol. 3, Ed. D. Barton and W. D. Ollis, Pergamon Press, Oxford, 1979, 311.
H. C. Clark and C. J. Willis,J. Am. Chem. Soc., 1960,82, 1888.
M. U. Bombala and S. V. Ley,J. Chem. Soc., Perkin Trans, 1, 1979, 3013.
M. V. Kalnins,Can. J. Chem., 1966,44, 2111.
V. I. Shcherbakov, I. K. Grigor'eva, O. S. D'yachkovskaya, and G. A. Razuvaev,Zh. Obshch. Khim., 1985,55, 107 [J. Gen. Chem. USSR, 1985,55 (Engl. Transl.)].
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2111–2114, December, 1993.
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Shcherbakov, V.I., Grigor'eva, I.K. Reactions of hexamethylditin and trimethyltin sulfide withN-thio-derivatives of phthalimide. Russ Chem Bull 42, 2025–2028 (1993). https://doi.org/10.1007/BF00698890
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DOI: https://doi.org/10.1007/BF00698890