Stable σh-adducts in the reactions of the acridinium cation with heterocyclic N-nucleophiles

Abstract

A reaction of NH-heterocycles with the 10-methylacridinium cation in the presence of a base led to 9,10-dihydro-10-methyl-9-substituted acridines, which can be considered as stable intermediates in the aromatic nucleophilic substitution reaction of hydrogen. The structure of the intermediates was studied and their oxidation potentials were determined. Generally, the oxidation potential was found to symbatically change with the changes in the energy of HOMO. © 2013 Springer Science+Business Media New York.