Reaction of organolithium reagents with α-chlorovinyltrimethylsilanes

The reaction of (CH₃)₃SiC(Cl)=CRR′ (R = R′ = H; R = H, R′ = CH₃; R = R′ = CH₃; R = R′ = C₆H₅) with organolithium, reagents was examined. Alkenylsilanes of structure (CH₃)₃SiCHCH-alkyl were obtained from (CH₃)₃SiC(Cl)CH₂ and alkyllithium reagents. Substrates with R or R′ ≠ H inhibited addition of the organolithium species to the double bond and led to products derived from chlorinelithium exchange (R = R′ = C₆H₅) or proton abstraction from an allylic methyl site (R = H, R′ = CH₃; R = R′ = CH₃).