ARKIVOC

The reaction of hydroxylamine with aspirin

…, BS Souza, ES Orth, TAS Brandão, W Rocha, AJ Kirby…

Index: Medeiros, Michelle; Souza, Bruno S.; Orth, Elisa S.; Brandao, Tiago A. S.; Rocha, Willian; Kirby, Anthony J.; Nome, Faruk Arkivoc, 2011 , vol. 2011, # 7 p. 461 - 476

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Abstract

Abstract Hydroxylamine reacts with aspirin in aqueous solution at 25 C predominantly through oxygen, to give O-acetylhydroxylamine as the initial product (Scheme 3). The reaction is much faster than the intramolecular general base catalysed hydrolysis of the carboxylate anion, as it is also for the CO2H form of aspirin. Both reactions are faster than expected, consistent with moderate activation and/or proton transfer catalysis of ...

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