An. Parker et L. Strekowski, An unusual 2,6-dialkoxylation of quinoline by the reaction with elemental fluorine and alcohol, HETEROCYC C, 4(6), 1998, pp. 493-496
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.