Tishchenko reaction

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search

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 Evgen'evich Tishchenko (Вячеслав Евгеньевич Тищенко).[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.
    • 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.
    • 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.
  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. ^ Kamm, O.; Kamm, W. F. (1941). "Benzyl benzoate". Organic Syntheses.; Collective Volume, 1, p. 104
  4. ^ Marc Eckert; Gerald Fleischmann; Reinhard Jira; Hermann M. Bolt; Klaus Golka (2007), "Acetaldehyde", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 4
  5. ^ Boy Cornils; Richard W. Fischer; Christian Kohlpaintner (2007), "Butanals", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 4
  6. ^ Peter Werle; Marcus Morawietz (2007), "Alcohols, Polyhydric", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 6
  7. ^ Günther Reuss; Walter Disteldorf; Armin Otto Gamer; Albrecht Hilt (2007), "Formaldehyde", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 5
  8. ^ Paul R. Stapp (1973). "Boric acid catalyzed Tishchenko reactions". J. Org. Chem. 38 (7): 1433–1434. doi:10.1021/jo00947a049.