A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russia.
Org Biomol Chem. 2019 Aug 28;17(34):7927-7937. doi: 10.1039/c9ob01689a.
The reaction of trimethyl(vinyl)silane with sulfonamides in the presence of N-bromosuccinimide was shown to proceed regioselectively in methylene chloride under mild conditions and led to the products of bromosulfamidation in up to 88% yield. The obtained adducts undergo base-promoted dehydrobromination to give 2-trimethylsilyl-N-sulfonyl aziridines in a close to quantitative yield. In the reaction with trifluoromethanesulfonamide in acetonitrile or tetrahydrofuran, the Ritter-type (solvent-interception) products were obtained and converted to 1-triflyl-2-methyl-5-(trimethylsilyl)-2-imidazoline or 4-triflyl-3-(trimethylsilyl)-1,4-oxazocane in almost quantitative yield.
三甲基（乙烯基）硅烷与磺酰胺在 N-溴代丁二酰亚胺存在下的反应，在温和条件下在二氯甲烷中进行，具有区域选择性，并以高达 88%的收率得到溴磺酰胺化产物。所得到的加成物在碱促进下进行脱氢溴化反应，以接近定量的产率得到 2-三甲基甲硅烷基-N-磺酰基氮丙啶。在与三氟甲磺酸酰胺在乙腈或四氢呋喃中的反应中，得到里特型（溶剂捕获）产物，并转化为几乎定量产率的 1-三氟甲基-2-甲基-5-（三甲基甲硅烷基）-2-咪唑啉或 4-三氟甲基-3-（三甲基甲硅烷基）-1,4-恶唑烷。
