SN2 substitution on sp2 nitrogen of protonated oxime

Article abstract of DOI:10.1246/cl.1998.111

Theoretical studies on intramolecular nucleophilic displacement of the prolonated oxime oxygen willi an aryl ring revealed that the substitution reaction on the sp² nitrogen atom is a low energy process. This seemingly anomalous substitution is due to the low-lying σ*-orbital of the O-protonated oxime. The theoretical conclusion received experimental support.