Acid-catalysed N–alkyl heterolysis of tertiary pyridinecarboxamides and benzamides under mild conditions

N Auzeil, M Largeron, MB Fleury

Index: Auzeil, Nicolas; Largeron, Martine; Fleury, Maurice-Bernard Journal of the Chemical Society. Perkin Transactions 2, 1999 , # 8 p. 1703 - 1709

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Citation Number: 15

Abstract

Tertiary pyridinecarboxamides 1–9 and related benzamides 10–18 bearing a tert-butyl substituent were found to undergo alkyl–nitrogen heterolysis under unusually mild conditions. Accordingly, the corresponding secondary amides 19–33 have been isolated in high yields as the sole reaction product. Through a kinetic study based on pH–rate profiles and activation parameters, we have shown that the alkyl–nitrogen fission involved an ...

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