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Fritsch-Buttenberg-Wiechell rearrangementThe Fritsch-Buttenberg-Wiechell rearrangement, named for Paul Ernst Moritz Fritsch, Wilhelm Paul Buttenberg, and Heinrich G. Wiechell, is a chemical reaction whereby a 1,1-diaryl-2-bromo-alkene rearranges to a 1,2-diaryl-alkyne by reaction with a strong base such as an alkoxide.[1][2][3][4] This rearrangement is also possible with alkyl substituents.[5] Additional recommended knowledge
Reaction MechanismThe strong base deprotonates the vinylic hydrogen, which after alpha-elimination forms a vinyl carbene. A 1,2-aryl migration forms the desired product, the 1,2-diaryl-alkyne. ScopeOne study explored this reaction for the synthesis of novel polyynes [6] [7]: References
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This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Fritsch-Buttenberg-Wiechell_rearrangement". A list of authors is available in Wikipedia. |