Title | Oxidation of alpha-Oxo-Oximes to Nitrile Oxides with Hypervalent Iodine Reagents |
Publication Type | Journal Article |
Year of Publication | 2011 |
Authors | Jen, T, Mendelsohn, BA, Ciufolini, MA |
Journal | JOURNAL OF ORGANIC CHEMISTRY |
Volume | 76 |
Pagination | 728-731 |
Date Published | JAN 21 |
ISSN | 0022-3263 |
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. |
DOI | 10.1021/jo102241s |