Efficient Preparation of Aldoximes from Arylaldehydes, Ethylenediamine and Oxone？ in Water.docVIP

Molecules 2007, 12, 231-236 molecules ISSN 1420-3049 Communication Efficient Preparation of Aldoximes from Arylaldehydes, Ethylenediamine and Oxone? in Water Jing-Jing Xia and Guan-Wu Wang* Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China * Author to whom correspondence should be addressed; E-mail: gwang@ Received: 25 January 2007; in revised form: 14 February 2007 / Accepted: 18 February 2007 / Published: 21 February 2007 Abstract: The one-pot reaction of aromatic aldehydes, ethylenediamine and Oxone? (2KHSO5·KHSO4·K2SO4) in pure water was found to unexpectedly afford aldoximes in excellent yields. Keywords: Aldoximes, aryl aldehydes, ethylenediamine, Oxone?, water Introduction Oximation has attracted intensive attention for several decades as an efficient method for characterization and purification of carbonyl compounds. Due to the nucleophilic character of oximes, they have been widely used for the preparation of a variety of nitrogen-containing compounds such as amides [1], hydroximinoyl chlorides [2], nitrones [3] and nitriles [4]. Oximes were usually prepared by the reaction of carbonyl compounds and hydroxylamine hydrochloride with adjustment of pH using a basic aqueous medium. Recently, some new techniques such as microwave irradiation [5] and solvent- free heating [6] were applied to this reaction. Oxidation of amines or hydroxylamines was another usual method for the synthesis of oximes [7]. On the other hand, the use of water as a reaction medium has attracted notable interest and offers a clean, economical and environmentally-safe protocol for many reactions [8]. In fact, more and more reactions have been reported to proceed smoothly and efficiently in water. In continuation of our interest in organic reactions in water [9], herein we report the unexpec