Stabilization of Unsymmetrically Annelated Imidazol-2-ylidenes with Respect to Their Higher Group 14 Homologues by n-/π-HOMO Inversion

Stabilization of Unsymmetrically Annelated Imidazol-2-ylidenes with Respect to Their Higher Group 14 Homologues by n-/π-HOMO Inversion

From annelation to an elation: The surprising stability of pyridoannelated imidazol‐2‐ylidenes (see scheme) in comparison with the heavier Group 14 homologues suggests broad tuning potential and control of the reactivity by the lone pair of electrons at the carbon atom. The asymmetric distribution o...

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Veröffentlicht in:Angewandte Chemie International Edition 2007-01, Vol.46 (15), p.2697-2700
Hauptverfasser: Ullah, Farman, Bajor, Gabor, Veszprémi, Tamas, Jones, Peter G., Heinicke, Joachim W.
Format: Artikel
Sprache:eng
Schlagworte:
carbenes
electronic structure
Electrons
Hydrocarbons - chemistry
Imidazoles - chemistry
imidazolium
Methane - analogs & derivatives
Methane - chemistry
Molecular Structure
photoelectron spectroscopy
Silanes - chemistry
silylenes
Spectrum Analysis
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Beschreibung
Zusammenfassung:From annelation to an elation: The surprising stability of pyridoannelated imidazol‐2‐ylidenes (see scheme) in comparison with the heavier Group 14 homologues suggests broad tuning potential and control of the reactivity by the lone pair of electrons at the carbon atom. The asymmetric distribution of π‐electron density, which destabilizes the heavier homologues, does not markedly diminish the kinetic stability of the N‐heterocyclic carbenes (NHCs).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200604516