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Synthesis of Epoxides from Alkyl Bromides and Alcohols with in Situ Generation of Dimethyl Sulfonium Ylide in DMSO Oxidations
- Source :
- The Journal of organic chemistry. 85(2)
- Publication Year :
- 2019
-
Abstract
- Direct conversion of the readily available alkyl bromides and alcohols to value-added epoxides using dimethyl sulfoxide (DMSO) under mild reaction conditions has been developed. Benzyl and allyl bromides, and activated and unactivated alcohols all proceeded smoothly to give epoxides in high to excellent yield. Dimethyl sulfide, generated by DMSO oxidations, was in situ elaborated to form the substituted dimethyl sulfonium ylide species that participates in the Corey-Chaykovsky epoxidation in a domino and one-pot fashion, respectively.
- Subjects :
- Reaction conditions
chemistry.chemical_classification
In situ
010405 organic chemistry
Dimethyl sulfoxide
Sulfonium
organic chemicals
Organic Chemistry
010402 general chemistry
01 natural sciences
Medicinal chemistry
0104 chemical sciences
chemistry.chemical_compound
chemistry
Ylide
Yield (chemistry)
Dimethyl sulfide
Alkyl
Subjects
Details
- ISSN :
- 15206904
- Volume :
- 85
- Issue :
- 2
- Database :
- OpenAIRE
- Journal :
- The Journal of organic chemistry
- Accession number :
- edsair.doi.dedup.....8b532c93fa0044ea8da45281cfcdf2d2