Allylic oxidations catalyzed by dirhodium caprolactamate via aqueous tert-butyl hydroperoxide: The role of the tert-butylperoxy radical

…, H Choi, K Wang, G Chiou, MP Doyle

Index: McLaughlin, Emily C.; Choi, Hojae; Wang, Kan; Chiou, Grace; Doyle, Michael P. Journal of Organic Chemistry, 2009 , vol. 74, # 2 p. 730 - 738

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Citation Number: 86

Abstract

Dirhodium (II) caprolactamate exhibits optimal efficiency for the production of the tert- butylperoxy radical, which is a selective reagent for hydrogen atom abstraction. These oxidation reactions occur with aqueous tert-butyl hydroperoxide (TBHP) without rapid hydrolysis of the caprolactamate ligands on dirhodium. Allylic oxidations of enones yield the corresponding enedione in moderate to high yields, and applications include allylic ...