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Synthesis 2008(13): 1979-1993
DOI: 10.1055/s-2008-1078445
DOI: 10.1055/s-2008-1078445
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Applications of TEMPO in Synthesis
Further Information
Received
3 March 2008
Publication Date:
11 June 2008 (online)
Publication History
Publication Date:
11 June 2008 (online)
Abstract
This review describes the broad application of TEMPO and its derivatives in organic synthesis. Various reactions including oxidation of alcohols, sulfides and organometallic compounds are discussed. Moreover, the use of TEMPO as a stoichiometric or catalytic cooxidant in various transition-metal-mediated reactions is presented. The application of TEMPO as a carbon-radical trapping reagent in cascade reactions is discussed. Finally, the review article focuses on the application of TEMPO-derived alkoxyamines as thermal carbon-radical precursors in synthesis and in polymer chemistry.
1 Nitroxides
2 Oxidations
2.1 Oxidation of Alcohols
2.2 Oxidation of Sulfides and Hydrogen Abstractions
3 TEMPO as Trapping Reagent
4 Reaction of TEMPO with Organometallic Compounds
5 Carbon-Oxygen Bond Homolysis of Alkoxyamines
6 Conclusions
Key words
nitroxides - oxidations - radical chemistry - domino reactions - polymerizations
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