Lemieux-Johnson oxidation

What is Lemieux-Johnson oxidation?

The oxidative cleavage of a carbon-carbon double bond resulting in the conversion of an olefin into two separate aldehydes was first reported by Lemieux and Johnson in 1956. This reaction is commonly known as the Lemieux-Johnson oxidative cleavage or simply the Lemieux-Johnson oxidation.

Lemieux-Johnson oxidation - general reaction scheme
Lemieux-Johnson oxidation

R1, R2 = H, alkyl, aryl

The reagent used for this reaction is a combination of osmium tetraoxide OsO4 and sodium periodate NaIO4, which is also referred to as the Lemieux-Johnson reagent.

Moreover, it is important to note that this reaction can also lead to the direct formation of a lactol from the oxidation of an olefin with a hydroxyl group close to the double bond.

The conversion of olefins to aldehydes can be effectively achieved through Lemieux-Johnson oxidation.

References

Notes – Osmium Tetroxide-Catalyzed Periodate Oxidation of Olefinic Bonds
R. Pappo, D. Allen, Jr., R. Lemieux, and W. Johnson
The Journal of Organic Chemistry 1956 21 (4), 478-479
DOI: 10.1021/jo01110a606

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