Interplay between an elusive 4-(isopropylamino)imidazol-2-ylidene and its isolable mesoionic tautomer, and associated reactivities

César, Vincent; Tourneux, Jean-Christophe; Vujkovic, Nadia; Brousses, Rémy; Lugan, Noël; Lavigne, Guy

Interplay between an elusive 4-(isopropylamino)imidazol-2-ylidene and its isolable mesoionic tautomer, and associated reactivities

2012

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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