The Swern oxidation is a commonly used synthetic method for the oxidation of primary and secondary alcohols to aldehydes and ketones respectively. Swern oxidation is generally conducted by an in situ generated sulfur ylide (1), produced by the reaction of oxalyl chloride with DMSO. Swern oxidations have advantages over other oxidation methods in its mildness, greater functional group tolerance, and minimized waste.
Reagents: DMSO, oxalyl chloride, triethylamine
Reactants: primary and secondary alcohols
Products: aldehydes, ketones
- 1)Synthesis of all of the four possible stereoisomers of 5-hydroxy-4-methyl-3-heptanone (sitophilure), the aggregation pheromone of the rice weevil and the maize weevil
- 2)Synthesis of 4,5-Benzotropones by Cyclization of 1,3-Bis-Silyl Enol Ethers with 1,2-Dialdehydes
- Oxidation of alcohols by “activated” dimethyl sulfoxide. a preparative, steric and mechanistic study
- Oxidation of Alcohols by Activated Dimethyl Sulfoxide and Related Reactions: An Update