Epoxidation of Strained Alkenes Catalysed by (1,2-dimethyl-4(1H)pyridinone-3-olate)2MnIIICl

Robinson-Miller, Adam, Wyatt, Mark and Tetard, David (2015) Epoxidation of Strained Alkenes Catalysed by (1,2-dimethyl-4(1H)pyridinone-3-olate)2MnIIICl. Journal of Molecular Catalysis A: Chemical, 398. pp. 376-390. ISSN 1381-1169

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Official URL: http://dx.doi.org/10.1016/j.molcata.2014.12.012

Abstract

The mild epoxidation of strained alkenes using (DMPO)2MnCl catalyst (DMPO = 1,2-dimethyl-4(1H)-pyridinone-3-olate) in the presence of various oxidants was studied. Hydrogen peroxide and monopersulfate were found to be the best oxidants when used with imidazole in acetonitrile at 4 °C, with up to 94% conversion. Dismutation of hydrogen peroxide was also observed when used as an oxidant. The epoxidation using hydrogen peroxide or monoperoxysulfate appears to be mild and very selective for strained alkenes. A mechanism is proposed where imidazole is required for activation of the oxidant and where a detected MnV = O species is proposed as the active species. Competitive reaction between H2O2 and the substrate for the active species is proposed and homolytic vs heterolytic scissions of the Osingle bondO bond of the oxidant are discussed.

Item Type: Article
Uncontrolled Keywords: epoxidation, manganese, hydroxypyridinone
Subjects: C900 Others in Biological Sciences
Department: Faculties > Health and Life Sciences > School of Life Sciences > Applied Sciences
Depositing User: Nicola King
Date Deposited: 26 Feb 2015 11:18
Last Modified: 24 May 2017 11:19
URI: http://nrl.northumbria.ac.uk/id/eprint/18504

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