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.
Isoxazole derivatives R 0240Oxidation of Oximes to Nitrile Oxides with Hypervalent Iodine Reagents. -Trapping of the nitrile oxides with alkenes and alkynes provides isoxazoline and isoxazole products. Intramolecular trapping is also possible to give fused systems. PhI(O-Ac)2 also promotes oxidative dearomatization of phenols which allows efficient one-pot synthesis of tricyclic isoxazolines starting from phenols like (XI). -(MENDELSON, B. A.; LEE, S.; KIM, S.; TEYSSIER, F.; AULAKH, V. S.; CIUFOLINI*, M. A.; Org. Lett. 11 (2009) 7, 1539-1542; Dep. Chem., Univ. British Columbia, Vancouver, B. C. V6T 1Z1, Can.; Eng.) -Jannicke 33-136
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