Favorskii reaction

The Favorskii reaction is an organic chemistry reaction between an alkyne and a carbonyl group, under basic conditions. The reaction was discovered in the early 1900s by the Russian chemist Alexei Yevgrafovich Favorskii.[1]

Favorskii reaction and the possible subsequent rearrangement
Favorskii reaction and the possible subsequent rearrangement

When the carbonyl is an aldehyde (R"=H), a rearrangement can occur to generate enone, although the secondary propargylic alcohol can be isolated in some cases.[2] When this rearrangement is catalyzed by an acid, it is called Meyer–Schuster rearrangement. When the base is sodium metal the reaction is called Nef synthesis.

  1. ^ Favorsky, A.E. (1905). "Action of potassium hydroxide on mixtures of ketones and phenylacetylene". Zhurnal Russkago Fiziko-Khimicheskago Obshchestva. 37: 643–645., Favorsky, A.E. (1907). "Action de la potasse caustique sur les mélanges des cétones avec le phénylacétylène". Bulletin de la Société Chimique de France. 2: 1087–1088.
  2. ^ Voronin, Vladimir V.; Ledovskaya, Maria S.; Bogachenkov, Alexander S.; Rodygin, Konstantin S.; Ananikov, Valentine P. (October 2018). "Acetylene in Organic Synthesis: Recent Progress and New Uses". Molecules. 23 (10): 2442. doi:10.3390/molecules23102442. PMC 6222752. PMID 30250005.