Nucleophilic displacements of N-aryl and heteroaryl groups. Part 8 . Intermolecular reactions of N-aryl-pyridinium, -quinolinium,and -acridinium salts with nucleophiles

N-Aryl-mono-, -tri- and -pentacyclic pyridinium cations react with S- and C-nucleophiles to give: (i) simple addition of hydride at the α-ring position, (ii) nucleophilic addition of thiophenoxide at the γ-ring position, (iii) deprotonation at the 6-position of a 5,6-dihydroquinolinium ring followed by prototropic shift to give a 1,2-dihydroquinoline derivative, (iv) ring contraction of a pyridine to a pyrrole ring, and (v) nucleophilic displacement of the N-aryl group.