Role of lactam vs. lactim tautomers in 2 (1 H)-pyridone catalysis of aromatic nucleophilic substitution

A Loppinet-Serani, F Charbonnier…

Index: Loppinet-Serani, Anne; Charbonnier, Florence; Rolando, Christian; Huc, Ivan Journal of the Chemical Society. Perkin Transactions 2, 1998 , # 4 p. 937 - 942

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Citation Number: 13

Abstract

3-Ethylaminocarbonyl-2 (1H)-pyridone 1 and 3-ethoxycarbonyl-2 (1H)-pyridone 2 have been synthesised and tested as catalysts for the aromatic nucleophilic substitution of fluoride by piperidine in 2-fluoro-5-nitrobenzonitrile 3. A kinetic model which takes into account the dimerisation of the catalysts has been developed, which allows a quantitative analysis of measured data. 3-Ethylaminocarbonyl-2 (1H)-pyridone 1 exists exclusively as a lactam ...