A Gas-phase Anionic Analog of the Wittig Reaction. An Ion Cyclotron Resonance Study of the Gas-phase Ion Chemistry of Silyl Carbanions

Article abstract of DOI:10.1002/oms.1210230907

Gas-phase ion-molecule reactions of a variety of fluorosilyl carbanions with compounds containing double bonds to oxygen, X=O, have been examined using pulsed ion cyclotron resonance spectroscopy.The predominant reaction channel observed for species not containing acidic hydrogen is a Wittig-like process involving Si-O bond formation and elimination of X=CH2 species.The gas-phase acidity of F3Si(CH3) has been determined and those of F2Si(CH3)2 and FSi(CH3)3 have been estimated.From the fluoride transfer reactions of F3SiCH2^- the fluoride affinity of F2Si=CH2 has been estimated and limits on the ? bond strength in this silaethene obtained.Potential analytical applications of the Wittig reactivity have been discussed.