DOI: 10.1039/d3qo00580a ISSN: 2052-4129
The “cobra effect” in the imidazolinone series: how a donor can disable the nucleophilicity
A. S. Gazizov, E. A. Kuznetsova, A. Z. Kamaletdinov, A. V. Smolobochkin, O. A. Lodochnikova, D. P. Gerasimova, A. R. Burilov, M. A. Pudovik- Organic Chemistry
Contrary to chemical intuition, electron-donating groups decrease the nucleophilicity of the double bond in imidazolin-2-ones, switching their reactivity from “enamide” to “base”. Enamide reactivity can be recovered by a careful choice of the catalyst and solvent.