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- Like Pfitzner–Moffatt oxidation and Swern oxidation, with DMSO, Ms2O can oxidize primary and secondary alcohols to aldehydes and ketones, respectively, in HMPA.
- Swern oxidation oxidises secondary alcohols into ketones using oxalyl chloride and dimethylsulfoxide. It also requires an organic base, such as triethylamine.
- 4 and Swern oxidation converted the alcohol group to the enone group in 1.5.
- This is of no consequence for stereocontrol because in the next step the alcohol is oxidized in a Swern oxidation to ketone 11.
- In organic chemistry, the Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol (...) is oxidized to an aldehyde (...) or ketone (...) using oxalyl chloride, dimethyl sulfoxide (DMSO) and an organic base, such as triethylamine.
- gives a 36% yield of propionaldehyde, and therefore for this type of reaction higher yielding methods using PCC or the Swern oxidation are recommended.
- The "Onodera reagent", a solution of P4O10 in DMSO, is employed for the oxidation of alcohols. This reaction is reminiscent of the Swern oxidation.
- Difluoro and monofluoro alcohols are more difficult to oxidize. Swern oxidation has been used, but a large excess of the oxidant had to be employed, and in some cases did not give reproducible results.
- The solution comprising DMSO and oxalyl chloride, followed by quenching with triethylamine converts alcohols to the corresponding aldehydes and ketones via the process known as the Swern oxidation.
- The reaction produces a secondary alcohol that then can be oxidized via the Swern oxidation.
- Dimethyl sulfoxide can produce an explosive reaction when exposed to acyl chlorides; at a low temperature, this reaction produces the oxidant for Swern oxidation.
- Reactions involving oxalyl chloride [...] (e.g., hydrolysis, reaction with carboxylic acids, Swern oxidation, etc.) often liberate both carbon dioxide and carbon monoxide via a fragmentation process.
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