Cannizzaro

Disproportionation of aromatic aldehydes into aromatic acids and aromatic alcohols.

The speed of the reaction depends on the substituents in the aromatic ring.

Crossing reaction (reaction of Rodionov and Fedorova) - using two different aldehydes (aromatic and aliphatic). Usually, fomaldehyde and alcohol are produced.

Intramolecular rearrangment reaction (also known as Cannizzaro's rearrangment) - transformation of alpha-ketoaldehydes into alpha-oxyacids.

Lock variant - transformation of aldehydes into acids using bases.

See also Tishtzenko.

Bibliography

• Cannizaro S., Ann., 1853, 88, 129.
• Lock G., Ber., 1930, 63, 855.
• Rodionov V. M., Fedorova A. M., ZhOH, 1937, 7, 947.
• Lachovicz D. R., Gritter R. J., J. Org. Chem., 1963, 28, 1061.
• Andreeva I. V. e.a., ZhPH, 1969, 42, 1857.
• Weigand-Hielgetag, 855.
• SOP, 2, 461.
• Ingold, 563.
• OR, 2, 106.