Hydrogen abstraction and electron transfer with aminoxyl radicals: Synthetic and mechanistic issues

Aminoxyl radicals (R2NO•) are a valuable class of reactive intermediates with interesting synthetic and reactivity properties. This Minireview summarizes salient synthetic results obtained in radical oxidations using aminoxyl radicals, and then focuses on reactivity issues arising from recent literature surveys. The structural and reactivity features of the aminoxyl radical and substrate provides a possible explanation of the double reactivity of the aminoxyl radicals. This mechanistic dichotomy between H-atom abstraction and electronabstraction routes is highlighted in this Minireview. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.