REACTION OF ORGANOLITHIUM REAGENTS WITH ALPHA-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)3SiCHCH-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 chlorinelithium exchange (R = R′ = C6H5) or proton abstraction from an allylic methyl site (R = H, R′ = CH3; R = R′ = CH3). © 1979.