Selective Synthesis of Unsymmetrical Peroxides: Transition-Metal-Catalyzed Oxidation of Malononitrile and Cyanoacetic Ester Derivatives by tert-Butyl Hydroperoxide at the α-Position

Abstract A novel method was developed for the selective oxidation of α-monosubstituted malononitrile and cyanoacetic ester derivatives at the α-position based on transition-metal-catalyzed reaction (Cu, Fe, Mn, Co) with TERT-butyl hydroperoxide giving unsymmetrical peroxides in 63-94% yields. The me...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2011-07, Vol.2011 (13), p.2091-2100
Main Authors: Terent’ev, Alexander O., Borisov, Dmitry A., Semenov, Vsevolod V., Chernyshev, Vladimir V., Dembitsky, Valery M., Nikishin, Gennady I.
Format: Article
Language:English
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Summary:Abstract A novel method was developed for the selective oxidation of α-monosubstituted malononitrile and cyanoacetic ester derivatives at the α-position based on transition-metal-catalyzed reaction (Cu, Fe, Mn, Co) with TERT-butyl hydroperoxide giving unsymmetrical peroxides in 63-94% yields. The method is facile, does not require large excesses of reagents, and is amenable to gram-scale synthesis.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0030-1260027