An unusual 2,6-dialkoxylation of quinoline by the reaction with elemental fluorine and alcohol

The one-step reaction produces 2,6-dimethoxyquinoline or 2,6-diethoxyquinol ine in 30-35% yields. The postulated mechanistic pathway involves the inter mediacy of a radical cation generated by single electron transfer from the initially formed 2-alkoxyquinoline to molecular fluorine or to 2-alkoxy-N-f luoroquinolinium cation.