Addition and deprotonation in reactions of hydroxide ion with a β-hydroxysilane

The reaction of hydroxide ion with a β-hydroxysilane, 2-trimethylsilylmethyl-2-propanol, has been studied in an ion cyclotron resonance Fourier transform mass spectrometer. Using labeled hydroxide, details of deprotonation of the hydroxyl group versus addition to silicon were established. The rate of deprotonation at the hydroxyl group is about one-half of addition to silicon.