The Journal of Organic Chemistry

Simple preparation of. alpha.-acyl. alpha.-arylthio oximes (N-hydroxy-2-oxoalkanimidothioates). Ambident reactivity of. alpha.-nitro ketones

ME Jung, DD Grove, SI Khan

Index: Jung, Michael E.; Grove, David D.; Khan, Saeed I. Journal of Organic Chemistry, 1987 , vol. 52, # 20 p. 4570 - 4573

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Citation Number: 10

Abstract

A one-step synthesis of a-acyl a-phenylthio oximes by nucleophilic dehydration of a-nitro ketones is described. Treatment of the a-nitro ketones 7a-c (prepared by reaction of the sodium salt of nitromethane 6 with the acylimidazoles 5a-c) with thiophenol and titanium tetrachloride in the presence of triethylamine gave the phenyl N-hydroxy-2- oxoalkanimidothioates 4a-c in good yield. These products are potentially useful ...