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Toward phenanthridin-2-ylidene: electrophilicity versus acidity in planar-constrained C-aryl iminium salts |
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| Authors: | Cattoën Xavier Bourissou Didier Bertrand Guy |
| Institution: | a Laboratoire Hétérochimie Fondamentale et Appliquée du CNRS (UMR 5069), Université Paul Sabatier, 118, route de Narbonne, 31062 Toulouse Cedex 9, France b UCR-CNRS Joint Research Chemistry Laboratory (UMR 2282), Department of Chemistry, University of California, Riverside, CA 92521-0403, USA |
| Abstract: | A phenanthridinium salt was prepared in four steps, including an intramolecular CH-arylation and a hydride abstraction reaction. Treatment with sterically demanding bases does not lead to the corresponding carbene, but rather to addition products: the planar-constrained geometry significantly enhances the electrophilicity over the acidity of C-aryl iminium salts. |
| Keywords: | Carbenes Nucleophilic addition Deprotonation Phenanthridinium salts Planar-constrained geometry |
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