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On the Use of Stable Organic Nitroxyl Radicals for the Oxidation of Primary and Secondary Alcohols

Synthesis · 1996 · Vol. 1996(10) · pp. 1153–1176

Arjan E. J. de Nooy✉(Delft University of Technology)Arie C. Besemer✉(Delft University of Technology)H. van Bekkum✉(Delft University of Technology)

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Abstract

This article reviews the oxidation of primary and secondary alcohols using nitroxyl radicals from the first publication in which this reaction was described in 1965. A variety of stoichiometric and catalytic methods is discussed, with reactions in organic solvents, under biphasic conditions as well as in water. Mechanistic studies and general experimental procedures are included. The high regioselectivity for the oxidation of primary alcohols that can be achieved in the presence of secondary alcohols is emphasised.

Oxidative Organic Chemistry Reactions Chemical Synthesis and Reactions Radical Photochemical ReactionsChemistryPrimary (astronomy)Alcohol oxidationNitroxylRadicalRegioselectivityOrganic chemistryCatalysisStoichiometryOrganic synthesis

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