ALUMINUM-CHLORIDE CATALYZED REGIOSELECTIVE ALLYLSILYLATION OF ALKENES- CONVENIENT ROUTE TO 5-SILYL-1-ALKENES

Allyltriorganosilanes react regioselectively with terminal or cyclic a lkenes in the presence of aluminum chloride catalyst under mild condit ions to afford 5-silyl-1-alkenes in good yield. In the allylsilylation of terminal alkenes the silyl group adds to the terminal carbon and t he allyl group to the inner carbon of the double bond and the reaction with cyclic olefins gives allylsilylated products having the silyl an d allyl groups in the trans position. This allylsilylation is a conven ient route to 5-silyl-1-alkenes. In the allylsilylations with the ster eohomogeneous (Z)-crotyltrimethylsilane, an allylic inversion is obser ved indicating a stepwise process of allylsilylation.