Bf. Bonini et al., CHEMISTRY OF SILYL THIOKETONES .10. SYNTHESIS AND REACTIVITY OF ALPHA-SILYL VINYL SULFIDES, Journal of the Chemical Society. Perkin transactions. I, (23), 1996, pp. 2803-2809
Aliphatic silyl thioketones containing an alpha-hydrogen atom undergo
enethiolization to Z-alpha-silyl enethiols 2. Compounds 2 react with a
variety of halides R(3)X to give open-chain alpha-silyl vinyl sulfide
s 3. Protiodesilylation of 3 was achieved upon treatment with fluoride
ion to give vinyl sulfides 4. Reaction of 3 with Grignard reagents, i
n the presence of an appropriate nickel catalyst, results in a series
of vinylsilanes 5 with a specific geometry.