Fritsch-Buttenberg-Wiechell rearrangement

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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.[1][2][3][4]

This rearrangement is also possible with alkyl substituents.[5]

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.

References

  1. Fritsch, P.; Ann. 1894, 279, 319.
  2. Buttenberg, W. P.; Ann. 1894, 279, 327.
  3. Wiechell, H.; Ann. 1894, 279, 332.
  4. Köbrich, G.; Angew. Chem. Int. Ed. 1965, 4, 49.
  5. Rezaei, H.; Yamanoi, S.; Chemla, F.; Normant, J. F. Org. Lett. 2000, 2, 419-421.

See also

ar:إعادة ترتيب فريتش-بوتينبرج-فايتشيل


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