Issue 17, 2012
From the journal:

Chemical Communications

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

Vincent César,*ab   Jean-Christophe Tourneux,ab   Nadia Vujkovic,ab   Rémy Brousses,ab   Noël Luganab  and  Guy Lavigne*ab  

* Corresponding authors

a CNRS, LCC (laboratoire de Chimie de Coordination), 205 route de Narbonne, F-31077 Toulouse Cedex 4, France
E-mail: Vincent.Cesar@lcc-toulouse.fr, Guy.Lavigne@lcc-toulouse.fr

b Université de Toulouse, UPS, INPT, 31077 Toulouse, France

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.

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

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Article information

DOI
https://doi.org/10.1039/C2CC17870B
Article type
Communication
Submitted
16 Dec 2011
Accepted
06 Jan 2012
First published
10 Jan 2012

Chem. Commun., 2012,48, 2349-2351

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

V. César, J. Tourneux, N. Vujkovic, R. Brousses, N. Lugan and G. Lavigne, Chem. Commun., 2012, 48, 2349 DOI: 10.1039/C2CC17870B

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