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 inJournal of the American Chemical Society Vol. 127; no. 50; pp. 17578 - 17579
Main Authors Marinescu, Lavinia, Mølbach, Merete, Rousseau, Cyril, Bols, Mikael
Format Journal Article
LanguageEnglish
Published Washington, DC American Chemical Society 21.12.2005
Subjects
Chemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Reactivity and mechanisms
Catalytic reaction
Hydrogen peroxide
Oligoholoside
Aniline derivatives
Experimental study
Macrocycle
Cyclodextrin
Homogeneous catalysis
Oxidative degradation
Reaction mechanism
Benzenic compound
Kinetic parameter
Rate constant
Catalyst activity
Primary amine
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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.
Bibliography:istex:EFD9A63A3E297F092B830D4DE3C963BD0FB9F0BD
ark:/67375/TPS-LF87H2R8-P
ObjectType-Article-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja054457q