Toward phenanthridin-2-ylidene: electrophilicity versus acidity in planar-constrained C-aryl iminium salts.
-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.
Cattoën
Xavier
X
Laboratoire Hétérochimie Fondamentale et Appliquée du CNRS (UMR 5069), Université Paul Sabatier, 118, route de Narbonne, 31062 Toulouse Cedex 9, France.
Bourissou
Didier
D
Bertrand
Guy
G
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