Oxidation of Oximes to Nitrile Oxides with Hypervalent Iodine Reagents

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• 作者：Brian A. Mendelsohn ; Shelley Lee ; Simon Kim ; Florian Teyssier ; Virender S. Aulakh ; Marco A. Ciufolini*
• 刊名：Organic Letters
• 出版年：2009
• 出版时间：April 2, 2009
• 年：2009
• 卷：11
• 期：7
• 页码：1539-1542
• 全文大小：148K
• 年卷期：v.11,no.7(April 2, 2009)
• ISSN：1523-7052

文摘

Iodobenzene diacetate in MeOH containing a catalytic amount of TFA efficiently oxidizes aldoximes to nitrile oxides. The latter may be trapped in situ with olefins in a bimolecular or an intramolecular mode. The new method enables the execution of tandem oxidative dearomatization of phenols/intramolecular nitrile oxide cycloaddition sequences leading to useful synthetic intermediates.