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DOI: 10.1039/A902521I (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1999, 1703-1710

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

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Nicolas Auzeil, Martine Largeron and Maurice-Bernard Fleury

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 initial protonation of the amide group that would concern the oxygen atom.

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