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Interplay between an elusive 4-(isopropylamino)imidazol-2-ylidene and its isolable mesoionic tautomer, and associated reactivities
Authors:César Vincent  Tourneux Jean-Christophe  Vujkovic Nadia  Brousses Rémy  Lugan Noël  Lavigne Guy
Affiliation:CNRS, LCC (laboratoire de Chimie de Coordination), 205 route de Narbonne, F-31077 Toulouse Cedex 4, France. Vincent.Cesar@lcc-toulouse.fr
Abstract:An elusive free 4-(isopropylamino)imidazol-2-ylidene is engaged in a tautomeric equilibrium with its mesoionic tautomer, 4-(isopropylamido)imidazolium, which displays the typical reactivity of a cyclic diaminocarbene; once coordinated to a Rh(I) centre, it undergoes a smooth 4e(-) oxidation of its backbone to yield an amido-amidino-carbene, a weak electron donor viable only in its complexed form.
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