Fritsch-Buttenberg-Wiechell rearrangement
From Biocrawler, the free encyclopedia.
The Fritsch-Buttenberg-Wiechell rearrangement 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.
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Reaction Mechanism
The strong base deprotonates the vinylic hydrogen, which after alpha-elimination forms a carbene. A 1,2-aryl migration forms the desired product, the 1,2-diaryl-alkyne.
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References
- Fritsch, P.; Ann. 1894, 279, 319.
- Buttenberg, W. P.; Ann. 1894, 279, 327.
- Wiechell, H.; Ann. 1894, 279, 332.
- Köbrich, G.; Angew. Chem. Int. Ed. 1965, 4, 49.
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See also
