10.1021/jo980604+
The research investigates a novel epoxidation method for olefins using in situ generated dimethyldioxirane under basic conditions. The purpose of this study is to develop a mild, efficient, and safe epoxidation procedure that can be used to prepare acid-sensitive epoxides. The key chemicals used in this research include olefins as substrates, acetone as the precursor for dimethyldioxirane, Oxone (potassium peroxymonosulfate) for generating dimethyldioxirane, and tetrabutylammonium hydrogen sulfate as a phase-transfer catalyst. The reactions are conducted at an apparent pH of 10.5-11.5, often in a CH3CN-dimethoxymethane solvent system, with potassium carbonate (K2CO3) used to maintain the basic environment. The study concludes that this epoxidation method is highly effective for a wide range of olefins, including those with terminal, trans, cis, and trisubstituted configurations, and it is compatible with various functional groups such as acetylenes, allyl silanes, and esters. The procedure is mild, safe, and economical, making it an attractive option for synthesizing epoxides, especially those that are acid-labile.