Albright-Goldman Oxidation

• 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.

• 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

• Reaction Mechanism

The basic mechanism is same as that of the original Swern oxidation.

• Examples

Example 1.^[1]

• Experimental Procedure

• Experimental Tips

• References

[1] Broka, C. A.; Gerlits, J. F. J. Org. Chem. 1988, 53, 2144. DOI: 10.1021/jo00245a002

• Related Books

[amazonjs asin=”0198556640″ locale=”US” title=”Oxidation and Reduction in Organic Synthesis (Oxford Chemistry Primers, 6)”] [amazonjs asin=”3527306420″ locale=”US” title=”Modern Oxidation Methods”] [amazonjs asin=”0387236074″ locale=”US” title=”Oxidation of Alcohols to Aldehydes and Ketones: A Guide to Current Common Practice (Basic Reactions in Organic Synthesis)”]

modified swern, oxidation of alcohols, synthesis of aldehydes, synthesis of ketones