Top Qs
Timeline
Chat
Perspective

Tishchenko reaction

Type of organic chemical reaction From Wikipedia, the free encyclopedia

Remove ads

The Tishchenko reaction is an organic chemical reaction that involves disproportionation of an aldehyde in the presence of an alkoxide. The reaction is named after Russian organic chemist Vyacheslav Tishchenko, who discovered that aluminium alkoxides are effective catalysts for the reaction.[1][2] [3]

Quick Facts Identifiers ...

In the related Cannizzaro reaction, the base is sodium hydroxide and then the oxidation product is a carboxylic acid and the reduction product is an alcohol.

Remove ads

History

The reaction involving benzaldehyde was discovered by Claisen using sodium benzylate as base.[1] The reaction produces benzyl benzoate.[4]

Thumb
The Tishchenko reaction: benzaldehyde reacts to benzyl benzoate, the catalyst is sodium benzylate.

Enolizable aldehydes are not amenable to Claisen's conditions. Vyacheslav Tishchenko discovered that aluminium alkoxides allowed the conversion of enolizable aldehydes to esters.

Remove ads

Examples

Remove ads

See also

References

Further reading

Loading related searches...

Wikiwand - on

Seamless Wikipedia browsing. On steroids.

Remove ads