Several manganese(III) porphyrin complexes were evaluated as catalysts in the oxidation of indane and tetralin with hydrogen peroxide, in the presence of ammonium acetate as a co-catalyst. Catalysis by Mn(Ill) meso-tetra-2,6-dichlorophenylporphyrins gave rise, in a first stage, to benzylic monooxygenation products (1-alcohols and 1-ketones). However, addition of excess of oxidant gave rise to overoxidation products and, in certain conditions, hydroxy-keto compounds were selectively obtained. Reactions catalysed by Mn(Ill) mesotetra-pentafluorophenylporphyrins showed higher capability to generate dehydrogenated products. As a result, 1H-indene and naphthalene were formed. To understand the reactions' pathway, the oxidations of 1-indanol, 1-indanone, 2-indanol, 1H-indene, 1-tetralol, 1-tetralone, 1,4-dihydroxytetralin and 4-hydroxy-1-tetralone were also considered with manganese (111) meso-tetra-2,6-dichlorophenylporphyiin chloride, Mn(TDCPP)Cl, as catalyst. (c) 2005 Elsevier B.V. All rights reserved.
Rebelo, S., Simoes, M., Neves, M., Silva, A., Tagliatesta, P., Cavaleiro, J. (2005). Oxidation of bicyclic arenes with hydrogen peroxide catalysed by Mn(III) porphyrins. JOURNAL OF MOLECULAR CATALYSIS. A: CHEMICAL, 232, 135-142 [10.1016/j.molcata.2005.01.042].
Oxidation of bicyclic arenes with hydrogen peroxide catalysed by Mn(III) porphyrins
TAGLIATESTA, PIETRO;
2005-01-01
Abstract
Several manganese(III) porphyrin complexes were evaluated as catalysts in the oxidation of indane and tetralin with hydrogen peroxide, in the presence of ammonium acetate as a co-catalyst. Catalysis by Mn(Ill) meso-tetra-2,6-dichlorophenylporphyrins gave rise, in a first stage, to benzylic monooxygenation products (1-alcohols and 1-ketones). However, addition of excess of oxidant gave rise to overoxidation products and, in certain conditions, hydroxy-keto compounds were selectively obtained. Reactions catalysed by Mn(Ill) mesotetra-pentafluorophenylporphyrins showed higher capability to generate dehydrogenated products. As a result, 1H-indene and naphthalene were formed. To understand the reactions' pathway, the oxidations of 1-indanol, 1-indanone, 2-indanol, 1H-indene, 1-tetralol, 1-tetralone, 1,4-dihydroxytetralin and 4-hydroxy-1-tetralone were also considered with manganese (111) meso-tetra-2,6-dichlorophenylporphyiin chloride, Mn(TDCPP)Cl, as catalyst. (c) 2005 Elsevier B.V. All rights reserved.Questo articolo è pubblicato sotto una Licenza Licenza Creative Commons
