Editing Swern oxidation (section)

{{short description|Organic redox reaction}}
{{Reactionbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 298094479
| Name = Swern oxidation
| Type = Organic redox reaction
| NamedAfter = [[Daniel Swern]]
| Section3 = {{Reactionbox Identifiers
   | OrganicChemistryNamed = swern-oxidation
   | RSC_ontology_id = 0000154
 }}
}}

In [[organic chemistry]], the '''Swern oxidation''' also known as '''Moffatt-Swern''', named after [[Daniel Swern]], is a [[chemical reaction]] whereby a primary or secondary [[Alcohol (chemistry)|alcohol]] ({{chem2|\sOH}}) is [[redox|oxidized]] to an [[aldehyde]] ({{chem2|\sCH\dO}}) or [[ketone]] ({{chem2|>C\dO}}) using [[oxalyl chloride]], [[dimethyl sulfoxide]] (DMSO) and an organic [[Base (chemistry)|base]], such as [[triethylamine]].<ref>{{cite journal | title = Oxidation of alcohols by "activated" dimethyl sulfoxide. A preparative, steric and mechanistic study | author = Omura, K.; [[Daniel Swern|Swern, D.]] | journal = [[Tetrahedron (journal)|Tetrahedron]] | year = 1978 | volume = 34 | issue = 11 | pages = 1651–1660 | doi = 10.1016/0040-4020(78)80197-5}}</ref><ref>{{cite journal | author = Mancuso, A. J.; Brownfain, D. S.; [[Daniel Swern|Swern, D.]] | title = Structure of the dimethyl sulfoxide-oxalyl chloride reaction product. Oxidation of heteroaromatic and diverse alcohols to carbonyl compounds | year = 1979 | journal = [[J. Org. Chem.]] | volume = 44 | issue = 23 | pages = 4148–4150 | doi = 10.1021/jo01337a028}}</ref><ref>{{cite journal | author = Mancuso, A. J.; Huang, S.-L.; [[Daniel Swern|Swern, D.]] | title = Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide "activated" by oxalyl chloride | year = 1978 | journal = [[J. Org. Chem.]] | volume = 43 | issue = 12 | pages = 2480–2482 | doi = 10.1021/jo00406a041}}</ref> It is one of the many oxidation reactions commonly referred to as 'activated DMSO' oxidations. The reaction is known for its mild character and wide tolerance of [[functional group]]s.<ref>{{OrgSynth | author = Dondoni, A.; Perrone, D. | title = Synthesis of 1,1-Dimethyl Ethyl-(''S'')-4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate by Oxidation of the Alcohol | collvol = 10 | collvolpages = 320 | year = 2004 | prep = v77p0064}}</ref><ref>{{OrgSynth | author = Bishop, R. | title = <nowiki>9-Thiabicyclo[3.3.1]nonane-2,6-dione</nowiki> | collvol = 9 | collvolpages = 692 | year = 1998 | prep = cv9p0692}}</ref><ref>{{OrgSynth | author = Leopold, E. J. | title = Selective hydroboration of a 1,3,7-triene: Homogeraniol | collvol = 7 | collvolpages = 258 | year = 1990 | prep = cv7p0258}}</ref><ref>{{cite book |author1=Tojo, G. |author2=Fernández, M. | title = Oxidation of alcohols to aldehydes and ketones: A guide to current common practice | publisher = Springer | year = 2006 | isbn = 0-387-23607-4}}</ref>

[[File:Swern Oxidation Scheme.png|center|400px|The Swern oxidation.]]

The by-products are [[dimethyl sulfide]] ((CH<sub>3</sub>)<sub>2</sub>S), [[carbon monoxide]] (CO), [[carbon dioxide]] (CO<sub>2</sub>) and—when triethylamine is used as base—[[triethylammonium chloride]] (Et<sub>3</sub>NHCl). Of the volatile by-products, dimethyl sulfide has a strong, pervasive odour and carbon monoxide is acutely toxic, so the reaction and the work-up needs to be performed in a fume hood. Dimethyl sulfide is a volatile liquid (B.P. 37&nbsp;°C) with an unpleasant odour at even low concentrations.<ref>{{cite journal | author = Mancuso, A. J.; [[Daniel Swern|Swern, D.]] | title = Activated dimethyl sulfoxide: Useful reagents for synthesis | journal = [[Synthesis (journal)|Synthesis]] | year = 1981 | volume = 1981 | issue = 3 | pages = 165–185 | doi = 10.1055/s-1981-29377 | type = Review}}</ref><ref>{{cite journal | author = Tidwell, T. T. | title = Oxidation of alcohols to carbonyl compounds via alkoxysulfonium ylides: The Moffatt, Swern, and related oxidations | journal = [[Org. React.]] | year = 1990 | volume = 39 | pages = 297–572 | doi = 10.1002/0471264180.or039.03 | isbn = 0471264180 | type = Review}}</ref><ref>{{cite journal | author = Tidwell, T. T. | title = Oxidation of alcohols by activated dimethyl sulfoxide and related reactions: An update | journal = [[Synthesis (journal)|Synthesis]] | year = 1990 | volume = 1990 | issue = 10 | pages = 857–870 | type = Review | doi = 10.1055/s-1990-27036}}</ref>