Abstract
The treatment of benzylphenylsulfone with tetrabutylammonium hydroxide results in the formation of the title compound tetrabutylammonium phenyl(phenylsulfonyl)methylide. An X-ray structural analysis of the racemate shows the presence of a chiral metal-free carbanion in the form of an intimate ion pair. Stabilization of the conformational enantiomer occurs by a three-point interaction with two of the α-methylene moieties of the tetrabutylammonium ion, CH···O hydrogen bonding being the driving force. The ion pair is capable of initiating the anionic polymerization of acrylates.
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