swern oxidation

The mild oxidation of primary or secondary alcohols to aldehydes or ketones with a mixture of oxalyl chloride, dimethylsulfoxide and triethylamine is called the Swern oxidation. reaction scheme The advantages of this method compared to chromium(VI) reagents such as Jones reagent or PCC are the use of less toxic substances and that a further oxidation to the carboxylic acid is not possible with these reagents. One problem is that the by-product (dimethyl sulfide) is a volatile liquid (B.P. 37 °C) with an unpleasant odour- so the work-up needs to be performed in a fume-cupboard (hood).

External link

Link to the detailed reaction mechanism: http://www.organic-chemistry.org/namedreactions/swern-oxidation.shtm

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