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Synthesis 1996; 1996(10): 1153-1176
DOI: 10.1055/s-1996-4369
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On the Use of Stable Organic Nitroxyl Radicals for the Oxidation of Primary and Secondary Alcohols

Arjan E. J. de Nooy, Arie C. Besemer, Herman van Bekkum*
  • *Delft University of Technology, Laboratory of Organic Chemistry and Catalysis, Julianalaan 136, NL-2628 BL, Delft, The Netherlands, Fax +31(15)2781415
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Publikationsdatum:
31. Dezember 2000 (online)

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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.

Catalytic and stoichiometric oxidation methods using nitroxyl radicals for a wide range of alcoholic substrates are reviewed.