Synthesis, Characterization, and Applications of Zwitterions Containing a Carbanion Moiety

Synthesis, Characterization, and Applications of Zwitterions Containing a Carbanion Moiety

A trifle of triflyl: N‐substituted anilines react with 1,1,3,3‐tetrakis(triflyl)propane to give a 2,2‐bis(triflyl)ethyl group at the para position of the ring. The product is a zwitterion with a carbanion and an ammonium moiety, and can be used as an acid catalyst for organic reactions (see scheme)....

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Veröffentlicht in:Angewandte Chemie International Edition 2013-01, Vol.52 (5), p.1560-1563
Hauptverfasser: Yanai, Hikaru, Yoshino, Tasuku, Fujita, Masaya, Fukaya, Haruhiko, Kotani, Akira, Kusu, Fumiyo, Taguchi, Takeo
Format: Artikel
Sprache:eng
Schlagworte:
aldol reaction
Aniline
Anions - chemistry
carbanions
Carbon - chemistry
Catalysts
Crystallography, X-Ray
homogeneous catalysis
Molecular Conformation
Quaternary Ammonium Compounds - chemistry
Rings (mathematics)
Synthesis
synthetic methodology
zwitterions
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Zusammenfassung:A trifle of triflyl: N‐substituted anilines react with 1,1,3,3‐tetrakis(triflyl)propane to give a 2,2‐bis(triflyl)ethyl group at the para position of the ring. The product is a zwitterion with a carbanion and an ammonium moiety, and can be used as an acid catalyst for organic reactions (see scheme).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201208809