Tishchenko reaction

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The Tishchenko reaction is an organic chemical reaction that involves disproportionation of an aldehyde in the presence of an alkoxide.[1] The reaction product is an ester. Catalysts are aluminium alkoxides or sodium alkoxides. It is named after the Russian organic chemist Vyacheslav Tishchenko.[2]

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.

Examples[edit]

The Tishchenko reaction: benzaldehyde reacts to benzyl benzoate, the catalyst is generated in situ from sodium and benzyl alcohol

Related reactions[edit]

References[edit]

  1. ^ See:
    • V. E. Tishchenko (1906), "О действии алкоголятов алюминия на альдегиды. Сложного-эфира конденсации, как новый вид уплотнения альдегида." [On the effect of aluminium alkoxides on aldehydes. Ester condensation, as a new kind of aldehyde condensation.], Журнал Русского Физико-Химического Общества (Journal of the Russian Physico-Chemical Society), 38: 355–418 ; 482–540. (in Russian)
    • В. Е. Тищенко and Г. Н. Григорьева (V. E. Tishchenko and G. N. Grigor'eva) (1906) "О действии амальгамы магния на изомасляного альдегида" (On the effect of magnesium amalgam on isobutyric aldehyde), Журнал Русского Физико-Химического Общества (Journal of the Russian Physico-Chemical Society), 38 : 540–547. (in Russian)
    • М. П. Воронҝова and В. Е. Тищенко (M. P. Voronkova and V. E. Tishchenko) (1906) "О действии амальгамы магния на уксусный альдегид" (On the effect of magnesium amalgam on acetic aldehyde), Журнал Русского Физико-Химического Общества (Journal of the Russian Physico-Chemical Society), 38 : 547–550. (in Russian)
  2. ^ В. Тищенко (V. Tishchenko) (1899) "Действие амальгамированного алюминия на алкоголь. Алкоголятов алюминия, их свойства и реакции." (Effect of amalgamated aluminium on alcohol. Aluminium alkoxides, their properties and reactions.), Журнал Русского Физико-Химического Общества (Journal of the Russian Physico-Chemical Society), 31 : 694–770. (in Russian)
  3. ^ a b Kamm, O.; Kamm, W. F. (1922). "Benzyl benzoate". Organic Syntheses. 2: 5. doi:10.15227/orgsyn.002.0005.; Collective Volume, 1, p. 104
  4. ^ Brühne, Friedrich; Wright, Elaine (15 October 2011). "Benzaldehyde". Ullmann's Encyclopedia of Industrial Chemistry. Wiley. doi:10.1002/14356007.a03_463.pub2.
  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.
  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.
  7. ^ Werle, Peter; Morawietz, Marcus (15 June 2000). "Alcohols, Polyhydric". Ullmann's Encyclopedia of Industrial Chemistry. Wiley. doi:10.1002/14356007.a01_305.
  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.
  9. ^ Paul R. Stapp (1973). "Boric acid catalyzed Tishchenko reactions". Journal of Organic Chemistry. 38 (7): 1433–1434. doi:10.1021/jo00947a049.