882-59-7Relevant articles and documents
Simple metal oxides as efficient heterogeneous catalysts for epoxidation of alkenes by molecular oxygen
Liang, Jun,Tang, Qinghu,Meng, Guanyu,Wu, Hongli,Zhang, Qinghong,Wang, Ye
, p. 1140 - 1141 (2004)
Magnetite iron oxide (Fe3O4) has been found to be an efficient heterogeneous catalyst for the epoxidation of alkenes by molecular oxygen in the absence of a sacrificial reductant among various transition metal oxides. The reaction probably proceeds via a radical mechanism.
Facile synthesis of libraries of functionalized cyclopropanes and oxiranes using ionic liquids – A new approach to the classical Corey-Chaykovsky reaction
Malunavar, Shruti S.,Sutar, Suraj M.,Prabhala, Pavankumar,Savanur, Hemantkumar M.,Kalkhambkar, Rajesh G.,Aridoss, Gopalakrishnan,Laali, Kenneth K.
supporting information, (2021/09/13)
The potential of [PAIM][NTf2]/BMIM-ILs as a base/solvent in the Corey-Chaykovsky reaction is demonstrated by the facile synthesis of libraries of functionalized cyclopropanes from enones and oxiranes from aldehydes and ketones, at room temperature in respectable isolated yields. To demonstrate their application, the synthesized epoxides were employed as substrates for the synthesis of a library of 2,3-disubstituted quinolines, using [BMIM(SO3H)][OTf]/[BMIM][PF6] as a catalyst/solvent. The potential for recycling/reuse of the IL solvents was also explored.
Retro-Corey-Chaykovsky Epoxidation: Converting Geminal Disubstituted Epoxides to Ketones
Li, Siqi,Li, Pingfan,Xu, Jiaxi
, (2019/09/13)
Corey-Chaykovsky epoxidation has been widely applied in the conversion of aldehydes and ketones to epoxides with sulfonium and sulfoxonium ylides. The reverse transformation is realized for conversion of geminal disubstituted epoxides to ketones in the presence of DABCO in refluxing mesitylene. The method is a weak basic transformation from epoxides to ketones with loss of a methylene group and can be applied as an alternative strategy of the acid-catalyzed Meinwald rearrangement or oxidation for conversion of epoxides to carbonyl compounds.
Continuous Flow Synthesis of Terminal Epoxides from Ketones Using in Situ Generated Bromomethyl Lithium
Von Keutz, Timo,Cantillo, David,Kappe, C. Oliver
supporting information, p. 10094 - 10098 (2019/12/24)
A scalable procedure for the direct preparation of epoxides from ketones has been developed. The method is based on the carefully controlled generation of (bromomethyl)lithium (LiCH2Br) from inexpensive CH2Br2 and MeLi in a continuous flow reactor. The reaction has shown excellent selectivity for a variety of substrates, including α-chloroketones, which typically fail under classic Corey-Chaykovsky conditions. This advantage has been used to develop a novel route toward the drug fluconazole.