Supramolecular Oxidation of Anilines Using Hydrogen Peroxide as Stoichiometric Oxidant

6A,6D-Di-O-(propan-2-on-1,3-diyl) α-cyclodextrin-6A,6D-dicarboxylate (2α) and 6A,6D-di-O-(propan-2-on-1,3-diyl) β-cyclodextrin-6A,6D-dicarboxylate (2β) were found to catalyze the oxidation of aromatic amines in the presence of hydrogen peroxide. The products were the corresponding nitro compounds or...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2005-12, Vol.127 (50), p.17578-17579
Main Authors: Marinescu, Lavinia, Mølbach, Merete, Rousseau, Cyril, Bols, Mikael
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Reactivity and mechanisms
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Summary:6A,6D-Di-O-(propan-2-on-1,3-diyl) α-cyclodextrin-6A,6D-dicarboxylate (2α) and 6A,6D-di-O-(propan-2-on-1,3-diyl) β-cyclodextrin-6A,6D-dicarboxylate (2β) were found to catalyze the oxidation of aromatic amines in the presence of hydrogen peroxide. The products were the corresponding nitro compounds or in some cases azo-, azoxy-, or other dimerization products. The catalysis was found to follow enzyme kinetics giving a rate increase (k cat/k uncat) of up to 1100 in the best case.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja054457q