Fritsch-Buttenberg-Wiechell rearrangement
- Fritsch-Buttenberg-Wiechell rearrangement
The 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.[cite journal ]
title = Ueber die Darstellung von Diphenylacetaldehyd und eine neue Synthese von Tolanderivaten
author = Paul Fritsch
journal = Justus Liebig's Annalen der Chemie
volume = 279
issue = 3
pages = 319–323
year = 1894
url =
doi = 10.1002/jlac.18942790310 ] [cite journal ]
title = Condensation des Dichloracetals mit Phenol und Toluol
author = Buttenberg, W. P.
journal = Justus Liebig's Annalen der Chemie
volume = 279
issue = 3
pages = 324–337
year = 1894
url =
doi = 10.1002/jlac.18942790311 ] [cite journal ]
title = Condensation des Dichloracetals mit Anisol und Phenetol
author = Wiechell, H.
journal = Justus Liebig's Annalen der Chemie
volume = 279
issue = 3
pages = 337–344
year = 1894
url =
doi = 10.1002/jlac.18942790312 ] [cite journal ]
title = Eliminations from Olefins
author = Köbrich, G.
journal = Angewandte Chemie International Edition
volume = 4
issue =
pages = 49–68
year = 1965
url =
doi = 10.1002/anie.196500491 ] This rearrangement is also possible with alkyl substituents.[cite journal ]
title = Fritsch-Buttenberg-Wiechell Rearrangement in the Aliphatic Series
author = Rezaei, H.; Yamanoi, S.; Chemla, F.; Normant, J. F.
journal = Org. Lett.
volume = 2
issue = 4
pages = 419–421
year = 2000
url =
doi = 10.1021/ol991117z ] Reaction Mechanism
The 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.
cope
One study explored this reaction for the synthesis of novel polyynes ["One-Pot Formation and Derivatization of Di- and Triynes Based on the Fritsch-Buttenberg-Wiechell Rearrangement" Thanh Luu, Yasuhiro Morisaki, Nina Cunningham, and Rik R. Tykwinski J. Org. Chem. 2007, 72, 9622-9629 DOI|10.1021/jo701810g] [The metal acetylide intermediate is captured by electrophile methyl iodide. The reaction product is a biomolecule found in for instance Bidens pilosa] :
References
ee also
*Corey-Fuchs reaction
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