Issue 3, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Selenium catalysed oxidations with aqueous hydrogen peroxide. Part I: epoxidation reactions in homogeneous solution

Gerd-Jan ten Brink,a   Bruno C. M. Fernandes,a   Michiel C. A. van Vliet,a   Isabel W. C. E. Arendsa  and  Roger A. Sheldon*a  

* Corresponding authors

a Laboratory for Organic Chemistry and Catalysis, Delft University of Technology, Julianalaan 136, Delft, The Netherlands
E-mail: secretariat-ock@tnw.tudelft.nl
Fax: +31-15-2781415
Tel: +31-15-2782683

Abstract

Several diselenides were synthesised and tested for catalytic activity in epoxidation reactions with aqueous hydrogen peroxide. Bis[3,5-bis(trifluoromethyl)phenyl] diselenide forms the corresponding 3,5-bis(trifluoromethyl)benzene seleninic acid (L. Syper and J. Mlochowski, Tetrahedron, 1987, 43, 207.) in situ, which is a highly reactive and selective catalyst for the epoxidation of olefins in 2,2,2-trifluoroethanol. This is the first selenium compound that effectively (substrate to catalyst molar ratio s/c = 200) catalyses the formation of sensitive epoxides in nearly quantitative yields.

Graphical abstract: Selenium catalysed oxidations with aqueous hydrogen peroxide. Part I: epoxidation reactions in homogeneous solution

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Article information

DOI
https://doi.org/10.1039/B008198L
Article type
Paper
Submitted
11 Oct 2000
Accepted
07 Dec 2000
First published
10 Jan 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 224-228

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Selenium catalysed oxidations with aqueous hydrogen peroxide. Part I: epoxidation reactions in homogeneous solution

G. ten Brink, B. C. M. Fernandes, M. C. A. van Vliet, I. W. C. E. Arends and R. A. Sheldon, J. Chem. Soc., Perkin Trans. 1, 2001, 224 DOI: 10.1039/B008198L

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