Oxidation with TFAA

Mild oxidation method used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones.

Swern Oxidation, a mild oxidation method used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones is able to use TFAA as an activator of DMSO. This method is costly and less effective than Oxalyl chloride but was a effective activator prior to the usage of oxalyl chloride.¹

Summary

The reaction entry summary. Find the general scheme and full summarized mechanisms here.

General Scheme

This section briefly summarizes what can and cannot undergo reactions.

• 1° Alcohols (Primary) get oxidized to Aldehydes.
• 2° Alcohols (Secondary) get oxidized to Ketones.
• 3° Alcohols (Tertiary) do not get oxidized at all.

General Mechanism

This section briefly summarizes steps to find the product and perform the mechanisms.

Quick steps to finding the product for any alcohol

1. Identify the reagents.
2. Assign side chains (non alcohol part).
3. Selectively convert Alcohol to correct product based on alcohol type. Nothing else.
4. Keep the side chains (non alcohol part) the same and piece together the full molecule together again.

Full Primary Alcohol to Aldehyde Mechanism

Full Secondary Alcohol to Ketone Mechanism

Always remember to repeatedly practice your mechanisms and getting your reagents correct. Take advantage of our materials and/or keep practicing on a whiteboard or paper until you get it right every single time.

References

1. Omura, K.; Swern, D. Oxidation of Alcohols by “Activated” Dimethyl Sulfoxide. A Preparative, Steric and Mechanistic Study. Tetrahedron 1978, 34 (11), 1651–1660. DOI: 10.1016/0040-4020(78)80197-5