Published TCIMAIL newest issue No.197
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Swern Oxidation
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 alcohols, Secondary alcohols
- Products:
- aldehydes, ketones
- Scheme:
-
- 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
- Original literature:
-
- Oxidation of alcohols by “activated” dimethyl sulfoxide. a preparative, steric and mechanistic study
- Review literature:
-
- Oxidation of Alcohols by Activated Dimethyl Sulfoxide and Related Reactions: An Update
