Kinetics and mechanism of bromination of 2-pyridinone and related derivatives in aqueous solution

OS Tee, M Paventi

Index: Tee, Oswald S.; Paventi, Martino Journal of the American Chemical Society, 1982 , vol. 104, # 15 p. 4142 - 4146

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Citation Number: 29

Abstract

Abstract: The tautomeric system 2-pyridone s 2-hydroxypyridine (la s 2a) reacts with aqueous bromine via the principal tautomer la at pH< 6 and via the conjugate anion at pH> 6. Attack upon la occurs preferentially at the 3 position, whereas reaction upon the anion probably involves major attack at the 5 position. The facile dibromination of 2-pyridone results from the comparable reactivity of the monobromopyridones at pH< 1 or pH> 4. ...