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Oxidation of Oximes to Nitrile Oxides with Hypervalent Iodine Reagents

TitleOxidation of Oximes to Nitrile Oxides with Hypervalent Iodine Reagents
Publication TypeJournal Article
Year of Publication2009
AuthorsMendelsohn, BA, Lee, S, Kim, S, Teyssier, F, Aulakh, VS, Ciufolini, MA
JournalOrganic Letters
Volume11
Pagination1539-1542
Date PublishedApr
Type of ArticleArticle
ISBN Number1523-7060
KeywordsAMIDATION, CARBONYL-COMPOUNDS, CHEMISTRY, CONVERSION, DESS-MARTIN PERIODINANE, DIRECTIONS, FR901483, PHENOLS, TOSYLATES, TOSYLHYDRAZONES
Abstract

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.

URL<Go to ISI>://000264622600020