Reactions in Water: Alkyl Nitrile Coupling Reactions Using Fenton’s Reagent

The coupling reaction of water-soluble alkyl nitriles using Fenton’s reagent (Fe(II) and H2O2) is described. The best metal for the reaction is iron(II), and the greatest yields are obtained when the concentration of the metal is kept low. Hydrogen-atom abstraction is selective, preferentially produ...

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Bibliographic Details
Published in:Journal of organic chemistry 2008-05, Vol.73 (9), p.3616-3618
Main Authors: Keller, Christopher L, Dalessandro, James D, Hotz, Richard P, Pinhas, Allan R
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Free radicals chemistry
Organic chemistry
Reactivity and mechanisms
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Summary:The coupling reaction of water-soluble alkyl nitriles using Fenton’s reagent (Fe(II) and H2O2) is described. The best metal for the reaction is iron(II), and the greatest yields are obtained when the concentration of the metal is kept low. Hydrogen-atom abstraction is selective, preferentially producing the radical α to the nitrile. In order to increase the production of dinitrile, in situ reduction of iron(III) to iron(II), using a variety of reducing agents, was investigated.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo7026905