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REACTIONS OF PYRIDIN-2-OL, PYRIDIN-3-OL, AND PYRIDIN-4-OL WITH PENTAFLUORO- AND PENTACHLOROPYRIDINE

Reza Ranjbar-Karimi, Tayebeh Davodian, Hossein Mehrabi
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Abstract


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, 1H, 13C, and 19F NMR spectroscopy, as well as elemental analysis and X-ray crystallography.


Keywords


chemeoselectivity; pentafluoropyridine; pentachloropyridine; hydroxypyridine; synthesis; aromatic nucleophilic substitution

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