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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| Published in | Journal of the American Chemical Society Vol. 127; no. 50; pp. 17578 - 17579 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Washington, DC
American Chemical Society
21.12.2005
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| Subjects | |
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| Abstract | 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. |
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| AbstractList | 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. 6A,6D-Di-O-(propan-2-on-1,3-diyl) alpha-cyclodextrin-6A,6D-dicarboxylate (2alpha) and 6A,6D-di-O-(propan-2-on-1,3-diyl) beta-cyclodextrin-6A,6D-dicarboxylate (2beta) 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 (kcat/kuncat) of up to 1100 in the best case. |
| Author | Marinescu, Lavinia Bols, Mikael Mølbach, Merete Rousseau, Cyril |
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| Cites_doi | 10.1021/jo9723467 10.1007/978-1-4612-2426-6 10.1016/j.molcata.2004.01.006 10.1021/ar000058i 10.1039/b410098k |
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| Keywords | 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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| References | Chan W.-K. (ja054457qb00003/ja054457qb00003_1) 2003; 68 Murray R. W. (ja054457qb00004/ja054457qb00004_1) 1996; 37 Coperet C. (ja054457qb00004/ja054457qb00004_3) 1998; 63 Dugas H. (ja054457qb00001/ja054457qb00001_1) 1996 For (ja054457qb00002/ja054457qb00002_1) 1998; 98 Rousseau C. (ja054457qb00003/ja054457qb00003_3) 2005; 2734 Neimann K. (ja054457qb00005/ja054457qb00005_1) 2001; 487 Murray R. W. (ja054457qb00005/ja054457qb00005_2) 1989; 54 Wolfenden R (ja054457qb00001/ja054457qb00001_2) 2001; 34 Rousseau C. (ja054457qb00003/ja054457qb00003_2) 2004; 2 Zhu Z. (ja054457qb00004/ja054457qb00004_2) 1995; 60 Horváth T. (ja054457qb00006/ja054457qb00006_1) 2004; 215 |
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| Title | Supramolecular Oxidation of Anilines Using Hydrogen Peroxide as Stoichiometric Oxidant |
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