The orientation in the base-catalyzed rearrangement of 3-substituted jV-(aryloxy)pyridinium tetrafluoroborates (5) to 2or 6-(2-hydroxyaryl)pyridines has been studied. A 3-methyl group directs exclusively to the 6-position while inductively electron-withdrawing substituents (Cl, Br, I, OMe, C02Me, COMe) direct mainly, if not exclusively, to C-2. The phenols derived from 3-C02Me derivatives cyclize spontaneously to the substituted pyrido[3,2djcoumarins (8) in useful yields, and that from the 3-COMe compound gives 10-hydroxy-10-methyl-6-nitropyrido[2,3-d]benzopyran (9). The 3-halo-2-(2-hydroxyaryl)pyridines cyclize to benzofuro[3,2-b]pyridines (10,

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