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.
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.