Publication Type Journal Article
Title Hydrocarbon oxygenation with Oxone catalyzed by complex [Mn2L2O3](2+) (L=1,4,7-trimethyl-1,4,7-triazacyclononane) and oxalic acid
Authors Georgiy B. Shul'pin Yuriy N. Koziov Lidia S. Shul?pina Armando J.L. Pombeiro
Groups CCC
Journal TETRAHEDRON
Year 2012
Month October
Volume 68
Number 41
Pages 8589-8599
Abstract Oxone (peroxysulphate) very efficiently oxidizes benzene to p-quinone (TON 1140) and alkanes to the corresponding alcohols and ketones (aldehydes) in aqueous acetonitrile 50 degrees C if catalytic amounts of complex [Mn2L2O3](2+) (L=1,4,7-trimethyl-1,4,7-triazacyclononane) and oxalic acid are present in the solution. In contrast to the similar reaction with H2O2, the alkane oxidation with Oxone does not afford the corresponding alkyl hydroperoxides. Phenol was quantitatively oxidized to a mixture of p-quinone and pyrocatechol (9:1 ratio). Cyclohexanol gave cyclohexanone (TON 400). The proposed mechanism includes the formation of an oxidizing species containing the Mn(V)=O fragment. A kinetic study demonstrated that an adduct of [Mn2L2O3](2+) and oxalic acid is formed in the initial stage. This adduct reacts with Oxone to generate the oxidizing species. (C) 2012 Elsevier Ltd. All rights reserved.
DOI http://dx.doi.org/10.1016/j.tet.2012.07.098
ISBN
Publisher
Book Title
ISSN 0040-4020
EISSN
Conference Name
Bibtex ID ISI:000308846100010
Observations
Back to Publications List