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The Corey-Fuchs reaction is a series of chemical reactions designed to transform an aldehyde into an alkyne. The reaction is named after its discoverers, American chemists Elias James Corey and Philip L. Fuchs.
By suitable choice of base, it is often possible to stop the reaction at the 1-bromoalkyne, a useful functional group for further transformation.
The Corey-Fuchs reaction is based on a special case of the Wittig Reaction, where the phosphorus ylide is formed from dibromocarbene. This carbene is generated in situ from the reaction of Triphenylphosphine and carbon tetrabromide.
The dibromoalkene reacts with butyllithium via deprotonation. Next, the resulting species ejects bromide through an beta-elimination pathway to produce the alkyne.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Corey-Fuchs_reaction". A list of authors is available in Wikipedia.|