Tetrabutylammonium phenyl(phenlylsulfonyl) methylide: A chiral metal-free "carbanion"

The treatment of benzylphenylsulfone with tetrabutylammonium hydroxide resu lts in the formation of the title compound tetrabutylammonium phenyl(phenyl sulfonyl)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 pa ir. Stabilization of the conformational enantiomer occurs by a three-point interaction with two of the alpha-methylene moieties of the tetrabutylammon ium ion, CH ... O hydrogen bonding being the driving force. The ion pair is capable of initiating the anionic polymerization of acrylates.