Reactions of pyridin-2-ol, pyridin-3-ol, and pyridin-4-ol with pentafluoro- and pentachloropyridine

Reactions of pentafluoro- and pentachloropyridines with pyridin-2-ol, pyridin-3-ol, and pyridin-4-ol are reported. Pyridin-4-ol yields product of attack at the nitrogen atom, while pyridin-3-ol reacts at the oxygen atom. Pyridin-2-ol reacts as an ambident nucleophile, providing a mixture of products arising from attack at both the oxygen and the nitrogen atoms. The structures of compounds were confirmed by IR spectroscopy, 1 H, 13 C, and 19 F NMR spectroscopy, as well as elemental analysis and X-ray crystallography.