Synthesis of a Delocalized Azepinium Ion and Investigation of Its Electrophilic Character

Abstract

An isolated example: The first π-delocalized azepinium ions 2 were generated from 2H-azepines 1 and fully characterized by NMR spectroscopy. The stability of the ions was investigated by ab initio calculations. Reaction with nucleophiles led to further support of the characterization of the ions by the selective formation of 2-substituted 2H-azepines.