Formation and reaction of OMnV species in the oxidation of phenolic substrates with H2O2 catalysed by the dinuclear manganese(IV) 1,4,7-trimethyl-1,4,7-triazacyclononane complex [MnIV2(μ-O)3(TMTACN)2](PF6)2

Bruce C. Gilbert; John R. Lindsay Smith; Antoni Mairata i Payeras; John Oakes

doi:10.1039/B315427K

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Formation and reaction of OMn^V species in the oxidation of phenolic substrates with H₂O₂ catalysed by the dinuclear manganese(iv) 1,4,7-trimethyl-1,4,7-triazacyclononane complex [Mn^IV₂(μ-O)₃(TMTACN)₂](PF₆)₂

Bruce C. Gilbert,*^a John R. Lindsay Smith,*^a Antoni Mairata i Payeras^a and John Oakes^b

Author affiliations

* Corresponding authors

^a University of York, Department of Chemistry, Heslington, UK

^b Unilever Research, Port Sunlight Laboratories, Quarry Road East, Bebington, Merseyside, UK

Abstract

The oxidation of phenolic substrates with H₂O₂ catalysed by [Mn^IV₂(μ-O)₃(TMTACN)₂](PF₆)₂1, (TMTACN, 1,4,7-trimethyl-1,4,7-triazacyclononane) has been investigated by use of ESI mass spectrometry. The role of the phenols as one-electron reductants and as co-ligands in the stabilisation and reaction of an intermediate O [double bond, length as m-dash] Mn^V species has been analysed and the presence of a variety of manganese species in solution has been explained. Our results lead to a proposed mechanism for the catalytic oxidation of phenols in this system.

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Article information

DOI: https://doi.org/10.1039/B315427K
Article type: Paper
Submitted: 01 Dec 2003
Accepted: 19 Feb 2004
First published: 18 Mar 2004

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Org. Biomol. Chem., 2004,2, 1176-1180

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Formation and reaction of OMn^V species in the oxidation of phenolic substrates with H₂O₂ catalysed by the dinuclear manganese(IV) 1,4,7-trimethyl-1,4,7-triazacyclononane complex [Mn^IV₂(μ-O)₃(TMTACN)₂](PF₆)₂

B. C. Gilbert, J. R. L. Smith, A. M. I. Payeras and J. Oakes, Org. Biomol. Chem., 2004, 2, 1176 DOI: 10.1039/B315427K

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Organic & Biomolecular Chemistry