Back Swernova oxidace Czech Swern-Oxidation German Oxidación de Swern Spanish اکسایش سوورن Persian Swern-hapetus Finnish Oxydation de Swern French חמצון סוורן HE Oksidasi Swern ID Ossidazione di Swern Italian スワーン酸化 Japanese
| Swern oxidation | |
|---|---|
| Named after | Daniel Swern |
| Reaction type | Organic redox reaction |
| Identifiers | |
| Organic Chemistry Portal | swern-oxidation |
| RSC ontology ID | RXNO:0000154 |
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In organic chemistry, the Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol (−OH) is oxidized to an aldehyde (−CH=O) or ketone (>C=O) using oxalyl chloride, dimethyl sulfoxide (DMSO) and an organic base, such as triethylamine.[1][2][3] 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 groups.[4][5][6][7]
The by-products are dimethyl sulfide ((CH3)2S), carbon monoxide (CO), carbon dioxide (CO2) and—when triethylamine is used as base—triethylammonium chloride (Et3NHCl). 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 °C) with an unpleasant odour at even low concentrations.[8][9][10]
- ^ Omura, K.; Swern, D. (1978). "Oxidation of alcohols by "activated" dimethyl sulfoxide. A preparative, steric and mechanistic study". Tetrahedron. 34 (11): 1651–1660. doi:10.1016/0040-4020(78)80197-5.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Mancuso, A. J.; Brownfain, D. S.; Swern, D. (1979). "Structure of the dimethyl sulfoxide-oxalyl chloride reaction product. Oxidation of heteroaromatic and diverse alcohols to carbonyl compounds". J. Org. Chem. 44 (23): 4148–4150. doi:10.1021/jo01337a028.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Mancuso, A. J.; Huang, S.-L.; Swern, D. (1978). "Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide "activated" by oxalyl chloride". J. Org. Chem. 43 (12): 2480–2482. doi:10.1021/jo00406a041.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Dondoni, A.; Perrone, D. (2004). "Synthesis of 1,1-Dimethyl Ethyl-(S)-4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate by Oxidation of the Alcohol". Organic Syntheses
{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 10, p. 320. - ^ Bishop, R. (1998). "9-Thiabicyclo[3.3.1]nonane-2,6-dione". Organic Syntheses; Collected Volumes, vol. 9, p. 692.
- ^ Leopold, E. J. (1990). "Selective hydroboration of a 1,3,7-triene: Homogeraniol". Organic Syntheses; Collected Volumes, vol. 7, p. 258.
- ^ Tojo, G.; Fernández, M. (2006). Oxidation of alcohols to aldehydes and ketones: A guide to current common practice. Springer. ISBN 0-387-23607-4.
- ^ Mancuso, A. J.; Swern, D. (1981). "Activated dimethyl sulfoxide: Useful reagents for synthesis". Synthesis (Review). 1981 (3): 165–185. doi:10.1055/s-1981-29377.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Tidwell, T. T. (1990). "Oxidation of alcohols to carbonyl compounds via alkoxysulfonium ylides: The Moffatt, Swern, and related oxidations". Org. React. (Review). 39: 297–572. doi:10.1002/0471264180.or039.03. ISBN 0471264180.
- ^ Tidwell, T. T. (1990). "Oxidation of alcohols by activated dimethyl sulfoxide and related reactions: An update". Synthesis (Review). 1990 (10): 857–870. doi:10.1055/s-1990-27036.
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