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Swern oxidation[1]
Reaction[2]
Primary or secondary alcohol
+
2 DMSO
+
Oxalyl chloride [3]
↓
Aldehyde or ketone
+
Dimethylsulfide
+
Carbon monoxide
+
Carbon dioxide
+
HCl (scavenged) [4]
Conditions[6]
Typical solvents DMSO, CH2Cl2
Temperature < −60 ºC[5]
Identifiers[7]
RSC ontology ID RXNO:0000154

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.[8][9][10] The reaction is known for its mild character and wide tolerance of functional groups.[11][12][13][14]


Box 2

[edit]
Esterification[15]
Reaction[16]
Alcohol
+
Acid
↓↑
Ester
+
Water (molecule)

References

[edit]
  1. ^ box blahblah
  2. ^ March blahblah
  3. ^ March, somewhere on a page.
  4. ^ Generally, triethylamine is used as a scavenger
  5. ^ The reaction between DMSO and oxalyl chloride at room temperature is reported to be explosive: Bishop (1992).
  6. ^ conditions blahblah
  7. ^ identifiers blahblah
  8. ^ Kanji Omura and Daniel Swern (1978). "Oxidation of alcohols by "activated" dimethyl sulfoxide. a preparative, steric and mechanistic study". Tetrahedron. 34: 1651. doi:10.1016/0040-4020(78)80197-5.)
  9. ^ A. J. Mancuso, D. S. Brownfain and D. Swern (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.
  10. ^ A. J. Mancuso, S.-L. Huang and D. Swern (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.
  11. ^ 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.
  12. ^ Bishop, R. (1998). "9-Thiabicyclo[3.3.1]nonane-2,6-dione". Organic Syntheses; Collected Volumes, vol. 9, p. 692.
  13. ^ Leopold, E. J. (1990). "Selective Hydroboration of a 1,3,7-Triene: Homogeraniol". Organic Syntheses; Collected Volumes, vol. 7, p. 258.
  14. ^ Gabriel Tojo and Marcos Fernández (2006). Oxidation of Alcohols to Aldehydes and Ketones: A Guide to Current Common Practice. Springer. ISBN 0387236074.
  15. ^ box blahblah
  16. ^ March blahblah


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