Beilstein J. Org. Chem.2020,16, 1234–1276, doi:10.3762/bjoc.16.107
-oxyl radicals, oximeradicals (or iminoxyl radicals) have been underestimated for a long time as useful intermediates for organic synthesis, despite the fact that their precursors, oximes, are extremely widespread and easily available organic compounds. Furthermore, oximeradicals are structurally
exceptional. In these radicals, the N–O• fragment is connected to an organic moiety by a double bond, whereas all other classes of N-oxyl radicals contain an R2N–O• fragment with two single C–N bonds. Although oximeradicals have been known since 1964, their broad synthetic potential was not recognized until
previous works regarding generation, structure, stability, and spectral properties of these N-oxyl radicals. The reactions of oximeradicals are classified into intermolecular (oxidation by oximeradicals, oxidative C–O coupling) and intramolecular. The majority of works are devoted to intramolecular
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Graphical Abstract
Figure 1:
Imine-N-oxyl radicals (IV) discussed in the present review and other classes of N-oxyl radicals (I–...