Many related cations are known involving substituted pyridines, e.g. picolines, lutidines, collidines.
Its salts are often insoluble in the organic solvent, so precipitation of the pyridinium leaving group complex is an indication of the progress of the reaction.
These pyridinium intermediates have been used as electrophiles in synthetic organic chemistry to build dearomatized congeners called dihydropyridines, as demonstrated in one example from Smith in 2021.
[5] Earlier, the same research group also delineated the rules surrounding regioselectivities associated with adding nucleophiles to pyridinium electrophiles with varying substituents.
[6] From a commercial perspective, an important pyridinium compound is the herbicide paraquat.