Nucleophilic Reactivities of Deoxy Breslow Intermediates: How Does Aromaticity Affect the Catalytic Activities of N-Heterocyclic Carbenes?

Angew.Chem.Int.Ed., 2012, 51, 6231-6235 published on 09.05.2012
Aromatic or nonaromatic? Kinetic investigations show that structurally analogous saturated and unsaturated N-heterocyclic carbenes have almost identical nucleophilic reactivities, while the corresponding deoxy Breslow intermediates differ dramatically.
TU München