caa a22 4500 47575929X CHVBK 20180406123546.0 cr unu---uuuuu 170329e20000901xx s 000 0 eng 10.1007/BF02495161 doi (NATIONALLICENCE)springer-10.1007/BF02495161 Iodosulfenylation of olefins with sulfenamides in the presence of metal iodides [Elektronische Daten] [N. Zyk, E. Beloglazkina, S. Sosonyuk, M. Bulanov, Yu. Chudinov] 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. Kluwer Academic/Plenum Publishers, 2000 iodosulfenylation nationallicence iodosulfides nationallicence metal iodides nationallicence sulfenamides nationallicence sulfenates nationallicence thiobisamines nationallicence dithiobisamines nationallicence electrophilic addition nationallicence Zyk N. Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899, Moscow, Russian Federation aut Beloglazkina E. Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899, Moscow, Russian Federation aut Sosonyuk S. Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899, Moscow, Russian Federation aut Bulanov M. Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899, Moscow, Russian Federation aut Chudinov Yu Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899, Moscow, Russian Federation aut Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/9(2000-09-01), 1557-1571 1066-5285 49:9<1557 2000 49 11172 https://doi.org/10.1007/BF02495161 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF02495161 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Zyk N. Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Beloglazkina E. Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Sosonyuk S. Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Bulanov M. Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Chudinov Yu Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899, Moscow, Russian Federation aut NATIONALLICENCE 773 0- Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/9(2000-09-01), 1557-1571 1066-5285 49:9<1557 2000 49 11172 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer