Overall Score4
- Generality
- Reagent Availability
- Experimental User Friendliness
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General Characteristics
The Swern-type oxidation of alcohols using acetic anhydride as the activator of DMSO. The reaction times are relatively long (12-24 h). This reaction is useful for the oxidation of sterically hindered positions.
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General References
・Albright, J. D.; Goldman, L. J. Am. Chem. Soc. 1965,87, 4214. DOI: 10.1021/ja01096a055
・Albright, J. D.; Goldman, L. J. Am. Chem. Soc. 1967,89, 2416. DOI: 10.1021/ja00986a031
・Review: Tidwell, T. T. Synthesis 1990, 857. DOI: 10.1055/s-1990-27036
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Reaction Mechanism
The basic mechanism is same as that of the original Swern oxidation.
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Examples
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Experimental Procedure
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Experimental Tips
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References
[1] Broka, C. A.; Gerlits, J. F. J. Org. Chem. 1988, 53, 2144. DOI: 10.1021/jo00245a002
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