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Favorskii reaction
The Favorskii reaction is the nucleophilic attack of a terminal alkyne with acidic protons on a carbonyl group.〔M. Smith, J. March, ''March's advanced organic chemistry'', Wiley-Interscience, 2001〕 The reaction was discovered in the early 1900s by the Russian chemist Alexei Yevgrafovich Favorskii.
When catalyzed by acid, this reaction is called the Meyer–Schuster rearrangement.
==Reaction mechanism==
A metal acetylide is formed in situ when an alkyne is treated with a strong bases such as a hydroxide or an alkoxide. The metal acetylide then reacts with an aldehyde or ketone to form a propargyl alcohol. When an α-hydrogen is present (as is the case when the carbonyl is an aldehyde), it will tautomerize to the corresponding enone.
This reaction is used to protect alkynes: the alkyne is either converted with acetone to a 2-hydroxyprop-2-yl-alkyne or a protected alkyne can be directly synthesized using the commercially available 2-methyl-3-butyn-2-ol as an the alkyne source. The protective group can be removed by heating the compound in a solution of potassium hydroxide in propan-2-ol (a retro-Favorskii reaction).〔T. Greene, P. Wuts, ''Protective groups in organic synthesis'', Wiley-Interscience, 1998〕
抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』
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