Nucleophilicity Parameters for Alkyl and Aryl Isocyanides

摘要

Alkyl and aryl isocyanides have a unique carbene-like structure with a formally divalent carbon atom. Their electronic structure can be represented by the resonance formula 1' and 1". They are readily accessible by a variety of methods and are important substrates for several useful synthetic transformations including the Passerini and Ugi reactions. Many of these reactions proceed by the attack of a carbon electrophile at the isocyano group, but there is only little information about the thermodynamics and kinetics of these reactions.