Safe and Scaleable Oxidation of Benzaldoximes to Benzohydroximinoyl Chlorides†

EC Hansen, M Levent, TJ Connolly

Index: Hansen, Eric C.; Levent, Mahmut; Connolly, Terrence J. Organic Process Research and Development, 2010 , vol. 14, # 3 p. 574 - 578

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Citation Number: 16

Abstract

Benzohydroximinoyl chlorides are useful precursors to nitrile oxides used in the preparation of various heterocycles via 1, 3-dipolar cycloadditions. These intermediates are typically accessed by oxidation of aldoximes using N-chlorosuccinimide. This simple and efficient reaction is highly exothermic and a significant induction period can be observed. The potential for a sudden and significant heat release makes large-scale reactions difficult to ...