Aerobic oxidation of N-alkylamides catalyzed by N-hydroxyphthalimide under mild conditions. Polar and enthalpic effects

F Minisci, C Punta, F Recupero, F Fontana…

Index: Minisci, Francesco; Punta, Carlo; Recupero, Francesco; Fontana, Francesca; Franco Pedulli, Gian Journal of Organic Chemistry, 2002 , vol. 67, # 8 p. 2671 - 2676

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Citation Number: 96

Abstract

The oxidation of N-alkylamides by O2, catalyzed by N-hydroxyphthalimide (NHPI) and Co (II) salt, leads under mild conditions to carbonyl derivatives (aldehydes, ketones, carboxylic acids, imides) whose distribution depends on the nature of the alkyl group and on the reaction conditions. Primary N-benzylamides lead to imides and aromatic aldehydes at room temperature without any appreciable amount of carboxylic acids, while under the same ...