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Iodosulfenylation of olefins with sulfenamides in the presence of metal iodides

  • Organic Chemistry
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Russian Chemical Bulletin Aims and scope

Abstract

Reactions of arylsulfenamides, arylsulfenates, thiobisamines, and dithiobisamines with olefins in the presence of zinc, tin(ii), tin(iv), antimony(iii), or magnesium iodides were investigated. In the case of cage olefins, the reactions afford mixtures of 1,2-iodosulfides and diiodides, the ratio between which depends on the type of iodine-containing Lewis acid. lodosulfides were obtained in the highest yields in the reactions of cage olefins upon activation with zinc or tin(ii) iodides. In the case of olefins prone to the Wagner—Meerwein rearragement (bicyclo[2.2.1]heptanes) or to the addition—elimination reaction (camphene), the corresponding products formed. A reaction mechanism is proposed.

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Authors and Affiliations

  1. Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899, Moscow, Russian Federation

    N. V. Zyk, E. K. Beloglazkina, S. E. Sosonyuk, M. N. Bulanov & Yu. B. Chudinov

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  1. N. V. Zyk
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  2. E. K. Beloglazkina
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  3. S. E. Sosonyuk
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  4. M. N. Bulanov
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  5. Yu. B. Chudinov
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Published inIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1569–1582, September, 2000.

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Zyk, N.V., Beloglazkina, E.K., Sosonyuk, S.E. et al. Iodosulfenylation of olefins with sulfenamides in the presence of metal iodides. Russ Chem Bull 49, 1557–1571 (2000). https://doi.org/10.1007/BF02495161

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  • DOI: https://doi.org/10.1007/BF02495161

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