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Tetrabutylammonium Phenyl(phenylsulfonyl)methylide: A Chiral Metal‐free “Carbanion”
Author(s) -
Reetz Manfred T.,
Hütte Stephan,
Goddard Richard
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199910)1999:10<2475::aid-ejoc2475>3.0.co;2-a
Subject(s) - carbanion , chemistry , sulfone , metal , stereochemistry , organic chemistry
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.