Substitution of a carbon with silicon in the allyl anion yields a molecule that is a silyl anion with a carbon-carbon double bond, 1 , in resonance with a carbon anion with a silicon-carbon double bond, 2  . We are interested in synthesizing a sila-allyl anion to investigate the resonance between the two structures.  We will present the optimization of the reaction of diphenyldichlorosilane with excess lithium and trimethylsilylchloride to form phenyl-tristrimethylsilylsilane and conversion of that to vinyl-tristrimethylsilylsilane as a high yield and rapid synthesis.In a second project, we have synthesized 1,3-di-tert-butyl-1,1,3,3-tetramethyl-2-vinyltrisilane.  We will report our efforts to form the conjugate anion of both precursors.

Resonance and the silicon - carbon double bond

243rd National Meeting (2012)

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