Swern Oxidation

Swern Oxidation

Swern Oxidation


Primary or Secondary alcohol is oxidized to an aldehyde or ketone respectively when treated with dimethyl sulfoxide (DMSO) activated by oxalyl chloride (COCl)2 at low temperatures (-78 to -60°C) followed with an organic base like triethyl amine. This reaction is called Swern Oxidation.
Swern Oxidation is truly an organic oxidation, making it much more environmental friendly than either chromium or manganese metal use. Oxalyl Chloride is toxic and this reaction may be somewhat exothermic, so other reagents (such as Cyanuric acid and dicyclohexylcarbiimide (DCCI)) have replaced oxallyl chloride in the Swern reaction.
Swern Oxidation

Mechanism of Swern Oxidation

Mechanism of  Swern Oxidation

Mechanism of Swern Oxidation when reagent cyanuric acid is used in lieu of Oxalyl Chloride.

Mechanism of  Swern Oxidation with cyanuric acid

Examples of Swern Oxidation

Examples of Swern Oxidation