53229-40-6Relevant articles and documents
Epoxidation of olefins by β-bromoalkoxydimethylsulfonium ylides
Majetich, George,Shimkus, Joel,Li, Yang
supporting information; experimental part, p. 6830 - 6834 (2011/03/18)
Olefins can be converted to their respective epoxides in a one-pot procedure by dissolving the olefin in anhydrous DMSO, adding NBS to the reaction mixture to generate a β-bromoalkoxydimethylsulfonium ylide, and then adding DBU to the reaction mixture. A large variety of alkenes were successfully epoxi-dized with yields largely dependent on the structure of the alkene. Most importantly, the facial selectivity of this one-pot process is the opposite of that observed when using traditional epoxidizing reagents. Electron-poor alkenes are not epoxidized under these conditions.
