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

2001/01/01 by Gerd‐Jan ten Brink, Bruno C. M. Fernandes, Michiel C. A. van Vliet +2 · 3 citations
Chemistry · Materials Science · Pharmacology, Toxicology and Pharmaceutics · #Crystal Structures and Properties #Organic Chemistry Cycloaddition Reactions #Organoselenium and organotellurium chemistry

paper · doi:10.1039/b008198l

openalex publication_date 2001/01/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/30

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.

Citations

• Olefin synthesis. Rate enhancement of the elimination of alkyl aryl selenoxides by electron-withdrawing substituents

Cited by

• Selenium-Catalyzed Oxidations with Aqueous Hydrogen Peroxide. 2. Baeyer−Villiger Reactions in Homogeneous Solution1
• Cyclic Seleninate Esters as Catalysts for the Oxidation of Sulfides to Sulfoxides, Epoxidation of Alkenes, and Conversion of Enamines to α-Hydroxyketones
• Seleninic acid [wikipedia]