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Date: 2-8-2019
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Date: 16-10-2020
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Date: 14-9-2018
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The Swern oxidation uses dimethylsulfoxide and oxalyl chloride, followed by addition of a base such as triethylamine. The actual oxidizing species in this reaction is the dimethylchlorosulfonium ion, which forms from dimethylsulfoxide and oxalyl chloride.
The mechanism is included below, for reference:
In the first stage dimethylsulfoxide (DMSO) reacts with oxalyl chloride to give an electrophilic sulfur compound, which collapses to give a chlorosulfonium ion, CO2 and CO.
In the second stage the alchohol reacts with the chlorosulfonium ion to give a new sulfonium salt and HCl.
In the final stage the base (Et3N) is added to deprotonate the salt, which then collapses to give the desired aldehyde or ketone and dimethyl sulfide.
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