Polymer-supported methyltrioxorhenium (MTO) systems are efficient catalysts for the oxidative functionalisation of cyclohexane and cyclopentane, derivatives with H2O2 as oxygen donor. Using poly (4-vinyl)pyridine and poly(4-vinyl)pyridine-N-oxide as MTO supports, cycloalkanol, cycloalkanediol, cycloalkanone and omega-hydroxy methyl ketone derivatives were obtained in different yields depending on the experimental conditions. Interestingly, cycloalkane dimers were selectively recovered in acceptable to good yields when the oxidation was performed with polystyrene-microencapsulated MTO catalyst. The EPR investigation suggests that the homolytic cleavage of the CH3-Re bond with formation of CH3 center dot radicals occurs inside the polystyrene capsule, indicating a possible role of methyl radical in the cycloalkane dimerisation pathway. (c) 2006 Published by Elsevier Ltd.

Bianchini, G., Crucianelli, M., Canevali, C., Crestini, C., Morazzoni, F., Saladino, R. (2006). Efficient and selective oxidation of methyl substituted cycloalkanes by heterogeneous methyltrioxorhenium-hydrogen peroxide systems. TETRAHEDRON, 62(52), 12326-12333 [10.1016/j.tet.2006.10.013].

Efficient and selective oxidation of methyl substituted cycloalkanes by heterogeneous methyltrioxorhenium-hydrogen peroxide systems

CANEVALI, CARMEN;MORAZZONI, FRANCA;
2006

Abstract

Polymer-supported methyltrioxorhenium (MTO) systems are efficient catalysts for the oxidative functionalisation of cyclohexane and cyclopentane, derivatives with H2O2 as oxygen donor. Using poly (4-vinyl)pyridine and poly(4-vinyl)pyridine-N-oxide as MTO supports, cycloalkanol, cycloalkanediol, cycloalkanone and omega-hydroxy methyl ketone derivatives were obtained in different yields depending on the experimental conditions. Interestingly, cycloalkane dimers were selectively recovered in acceptable to good yields when the oxidation was performed with polystyrene-microencapsulated MTO catalyst. The EPR investigation suggests that the homolytic cleavage of the CH3-Re bond with formation of CH3 center dot radicals occurs inside the polystyrene capsule, indicating a possible role of methyl radical in the cycloalkane dimerisation pathway. (c) 2006 Published by Elsevier Ltd.
Articolo in rivista - Articolo scientifico
heterogeneous catalysis; methyltrioxorhenium; radical reactions; EPR spectroscopy
English
25-dic-2006
62
52
12326
12333
none
Bianchini, G., Crucianelli, M., Canevali, C., Crestini, C., Morazzoni, F., Saladino, R. (2006). Efficient and selective oxidation of methyl substituted cycloalkanes by heterogeneous methyltrioxorhenium-hydrogen peroxide systems. TETRAHEDRON, 62(52), 12326-12333 [10.1016/j.tet.2006.10.013].
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/23875
Citazioni
  • Scopus 26
  • ???jsp.display-item.citation.isi??? 27
Social impact