Synthesis and Reaction of Super Anions

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<^1H> NMR indicates that a mixture of phenyl trimethylsilyl ether and tris(diethyl-amino) sulfonium (TAS) difluorotrimethylsiliconate in THF exists in a dynamic equilibrium with TAS phenoxide and fluorotrimethylsilane. Evacuation of the volatile fluorosilane gives TAS phenoxide as air-sensitive crystals. This is also the case with an enol trimethylsilyl ether of benzyl methyl ketone, allowing the preparation of the TAS enolate. The conductivity measurement and the <^1H> and <^(13)C> NMR study have revealed the ionic nature of the TAS phenoxide and enolate in THF. These species display unique stereo-, chemo-, and regioselectivities in the nucleophilic reactions.