5811-94-9Relevant academic research and scientific papers
Bipyridine N,N'-dioxide: A felicitous ligand for methyltrioxorhenium- catalyzed epoxidation of olefins with hydrogen peroxide
Nakajima, Makoto,Sasaki, Yuka,Iwamoto, Hatsue,Hashimoto, Shun-Ichi
, p. 87 - 88 (2007/10/03)
Methyltrioxorhenium-catalyzed oxidation of olefins with hydrogen peroxide in the presence of bipyridine N.N'-dioxide gave epoxides in high yields, with no sign of formation of hydrolyzed diols.
Catalytic Epoxidation of Alkenes with Oxone
Denmark, Scott E.,Forbes, David C.,Hays, David S.,DePue, Jeffrey S.,Wilde, Richard G.
, p. 1391 - 1407 (2007/10/02)
A practical, general and efficient protocol for the catalytic epoxidation of alkenes has been developed.The in situ generation of reactive dioxiranes capable of epoxidizing a variety of alkenes under biphasic conditions has been accomplished using phase transfer catalysts bearing a carbonyl group.Optimal epoxidation conditions employ 10 mol percent of 1-dodecyl-1-methyl-4-oxopiperidinium triflate (8d(+)OTf(-)) in a CH2Cl2/pH 7.5-8.0 biphase using potassium monoperoxosulfate (Oxone) as the oxidant.Optimization of the conditions identified (1) slow addition rate, (2) pH 7.5-8.0, (3) N-dodecyl chain, and (4) the triflate salt as key experimental and structural variables.A selection of nine olefins was successfully oxidized to the corresponding epoxides in 83-96percent yield.
