Lithium, [2-(trimethylsilyl)ethenyl]-, (E)-

The Uses of Lithium, [2-(trimethylsilyl)ethenyl]-, (E)-

(E)-2-(Trimethylsilyl)vinyllithium is used for introduction of the β-(trimethylsilyl)vinyl moiety; the resulting alkenylsilanes undergo useful electrophilic substitutions of the TMS group. It takes part in the reactions of Substitution Reactions, Addition Reactions, etc.

Preparation

Attempts to produce synthetically useful quantities of (E)-2-(trimethylsilyl)vinyllithium (1) by reaction of lithium metal with (2-bromovinyl)trimethylsilane (2) failed because of concomitant metalation¨Celimination processes involving (1) and (2).2 However, the transmetalation process between (2) and excess t-butyllithium has been effectively used to provide (1) (eq 1).3 An alternative route to (1) employs the transmetalation of a 1-(trimethylsilyl)-2-stannylethylene with organolithium reagents (eqs 2 and 3).