Orthogonal reactivity of thiols toward chlorovinylsilanes: selective thiol-ene chemistry

A variety of new chlorosilanes were synthesized by the selective thiol-ene reactions of various thiols (ethanethiol, 1,2-ethanedithiol, benzenethiol, and tetrakis(2-sulfanylethyl)silicate) with chlorovinylsilanes (chlorodimethylvinylsilane, dichloromethylvinylsilane, and trichlorovinylsilane). No silylthioester products were observed. All products were obtained in quantitative or near quantitative yields and were characterized using multinuclear NMR (1H, 13C, 29Si) spectroscopy. The products required no further purification. An example is presented which highlights the potential use of these compounds for future applications.