OXYGENATION OF THE UNACTIVATED PYRIDINE SYSTEM BY ACETYL HYPOFLUORITE MADE DIRECTLY FROM F2

Article abstract of DOI:10.3987/COM-88-S5

Acetyl hypofluorite was found capable of activating the usually unreactive pyridine by substituting the hydrogen at the 2 position by an acetoxy group which then was hydrolyzed to the corresponding pyridinone.Substitutents at 3, 4 or 5 position do not interfere with the reaction, but compounds with substituents at 2 (with the exception of aromatic ones) either do not react or produce tars.The reaction conditions are very mild and the yields are very good for this kind of substitution.Quinolines and pyrazines also react very satisfactorily.