Oppenauer oxidation

What is Oppenauer oxidation?

Oppenauer oxidation is an organic chemical reaction in which an alcohol is oxidized to an aldehyde or ketone through the use of a transition metal catalyst, such as copper or chromium, and a reagent that can provide oxygen, such as air or hydrogen peroxide. The reaction was discovered by the German chemist Ernst Oppenauer in 1913 and is named after him..

Oppenauer oxidation
Oppenauer oxidation

Oppenauer oxidation typically proceeds through an intermediate called an “alkoxyl radical,” which is a reactive species that is formed when the alcohol is cleaved by the transition metal catalyst. The intermediate can then react with oxygen or another oxygen-containing species to produce the final aldehyde or ketone product..

One of the key features of the Oppenauer oxidation is that it allows for the synthesis of aldehydes and ketones from alcohols, which can be useful for synthesizing a wide range of compounds for various applications. Aldehydes and ketones are also important intermediates in a number of chemical reactions and can serve as starting materials for the synthesis of other compounds..

Oppenauer oxidation can be performed under a variety of conditions, including both acidic and basic conditions. The choice of conditions depends on the specific reactants and desired product, and can be influenced by factors such as the stability of the intermediate and the ability to control the regiochemistry of the reaction..

Summary

The Oppenauer oxidation is a useful tool for synthesizing aldehydes and ketones and has a wide range of applications in the field of organic chemistry..

References

Oppenauer, R.V. (1937), Eine Methode der Dehydrierung von Sekundären Alkoholen zu Ketonen. I. Zur Herstellung von Sterinketonen und Sexualhormonen. [A method of dehydration of secondary alcohols to ketones. I. For the preparation of sterol ketones and sex hormones.] Recl. Trav. Chim. Pays-Bas, 56: 137-144. https://doi.org/10.1002/recl.19370560206

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