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

Vincent César (1, 2) , Jean-Christophe Tourneux (1, 2) , Nadia Vujkovic (1, 2) , Rémy Brousses (1, 2) , Noël Lugan (1, 2) , Guy Lavigne (1, 2)

1 LCC - Laboratoire de chimie de coordination
2 UT3 - Université Toulouse III - Paul Sabatier

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.

Domains: Coordination chemistry

Vincent César, Jean-Christophe Tourneux, Nadia Vujkovic, Rémy Brousses, Noël Lugan, et al.. Interplay between an elusive 4-(isopropylamino)imidazol-2-ylidene and its isolable mesoionic tautomer, and associated reactivities. Chemical Communications, 2012, 48 (17), pp.2349. ⟨10.1039/C2CC17870B⟩. ⟨hal-02909453⟩