Tishchenko reaction

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Tishchenko reaction
Named after Vyacheslav Tishchenko
Reaction type Organic redox reaction
Identifiers
Organic Chemistry Portal tishchenko-reaction

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]

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.

History[edit]

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

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

Examples[edit]

See also[edit]

References[edit]

  1. ^ a b Seki, Tsunetake; Nakajo, Tetsuo; Onaka, Makoto (2006). "The Tishchenko Reaction: A Classic and Practical Tool for Ester Synthesis". Chemistry Letters. 35 (8): 824–829. doi:10.1246/cl.2006.824.
  2. ^ Mlynarski, Jacek (2006). "Direct Asymmetric Aldol-Tishchenko Reaction". European Journal of Organic Chemistry. 2006 (21): 4779–4786. doi:10.1002/ejoc.200600258.
  3. ^ Hattori, Hideshi (2001). "Solid base catalysts: Generation of basic sites and application to organic synthesis". Applied Catalysis A: General. 222 (1–2): 247–259. doi:10.1016/S0926-860X(01)00839-0.
  4. ^ Kamm, O.; Kamm, W. F. (1922). "Benzyl benzoate". Organic Syntheses. 2: 5. doi:10.15227/orgsyn.002.0005.
  5. ^ Eckert, Marc; Fleischmann, Gerald; Jira, Reinhard; Bolt, Hermann M.; Golka, Klaus (15 December 2006). "Acetaldehyde". Ullmann's Encyclopedia of Industrial Chemistry. Wiley. doi:10.1002/14356007.a01_031.pub2. ISBN 3527306730.
  6. ^ Cornils, Boy; Fischer, Richard W.; Kohlpaintner, Christian (15 September 2000). "Butanals". Ullmann's Encyclopedia of Industrial Chemistry. Wiley. doi:10.1002/14356007.a04_447. ISBN 3527306730.
  7. ^ Werle, Peter; Morawietz, Marcus (15 June 2000). "Alcohols, Polyhydric". Ullmann's Encyclopedia of Industrial Chemistry. Wiley. doi:10.1002/14356007.a01_305. ISBN 3527306730.
  8. ^ Reuss, Günther; Disteldorf, Walter; Gamer, Armin Otto; Hilt, Albrecht (15 June 2000). "Formaldehyde". Ullmann's Encyclopedia of Industrial Chemistry. Wiley. doi:10.1002/14356007.a11_619. ISBN 3527306730.
  9. ^ Paul R. Stapp (1973). "Boric acid catalyzed Tishchenko reactions". Journal of Organic Chemistry. 38 (7): 1433–1434. doi:10.1021/jo00947a049.

Further reading[edit]