Resonance and the Silicon-Carbon Double Bond

Presentation Type

Poster/Portfolio

Presenter Major(s)

Chemistry

Mentor Information

Randy Winchester

Department

Chemistry

Location

Kirkhof Center KC 79

Start Date

11-4-2012 9:00 AM

Keywords

Physical Science

Abstract

The allyl anion [CH2-CH=CH2](-) has been the subject of much research, and measurements of the barrier for rotation in the allyl anion provide a measure of the resonance stabilization of this molecule. Substitution of a carbon with silicon in the allyl anion yields a molecule that is a silyl anion, [SiH2-CH=CH2](-), with a carbon-carbon double bond in resonance with a carbon anion with a silicon-carbon double bond [CH2-CH=SiH2](-). We report optimization of the reaction of diphenyldichlorosilane with excess lithium and trimethylsilylchloride to form phenyl-tristrimethylsilylsilane and conversion of that to vinyltristrimethylsilylsilane as a high yield and rapid route to this silane. The results of our studies of the reaction of the vinylsilane with potassium tert-butoxide will be discussed.

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Apr 11th, 9:00 AM

Resonance and the Silicon-Carbon Double Bond

Kirkhof Center KC 79

The allyl anion [CH2-CH=CH2](-) has been the subject of much research, and measurements of the barrier for rotation in the allyl anion provide a measure of the resonance stabilization of this molecule. Substitution of a carbon with silicon in the allyl anion yields a molecule that is a silyl anion, [SiH2-CH=CH2](-), with a carbon-carbon double bond in resonance with a carbon anion with a silicon-carbon double bond [CH2-CH=SiH2](-). We report optimization of the reaction of diphenyldichlorosilane with excess lithium and trimethylsilylchloride to form phenyl-tristrimethylsilylsilane and conversion of that to vinyltristrimethylsilylsilane as a high yield and rapid route to this silane. The results of our studies of the reaction of the vinylsilane with potassium tert-butoxide will be discussed.