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Oxidation of alpha-Oxo-Oximes to Nitrile Oxides with Hypervalent Iodine Reagents

TitleOxidation of alpha-Oxo-Oximes to Nitrile Oxides with Hypervalent Iodine Reagents
Publication TypeJournal Article
Year of Publication2011
AuthorsJen, T, Mendelsohn, BA, Ciufolini, MA
JournalJOURNAL OF ORGANIC CHEMISTRY
Volume76
Pagination728-731
Date PublishedJAN 21
ISSN0022-3263
Abstract

Upon reaction with PhI(OAc)(2), alpha-oxo-aldoximes are oxidized to alpha-oxo-nitrile oxides, while alpha-oxo-ketoximes are converted into nitrile oxides via the oxidative cleavage of the carbonyl-imino sigma bond. The nitrile oxides thus formed were trapped with norbornene or styrene in good yield. alpha,alpha'-Dioxo-ketoximes react less efficiently.

DOI10.1021/jo102241s