The halogen dance rearrangement is an organic reaction in which a halogen substituent moves to a new position on an aromatic ring system.[1] The reaction belongs to a class of organic reactions called 1,2-rearrangements. The original halogen dance is the base-catalysed rearrangement of 1,2,4-tribromobenzene to 1,3,5-tribromobenzene in liquid ammonia with the aniline/potassium base system. The intermediate in this reaction is an aryl carbanion. The halogen dance concept can be extended from benzene derivatives to other aromatic systems as well, for instance furan[2] and thiophene[3] compounds.

The halogen dance rearrangement of iodooxazoles was studied by the Stambuli Group.[4]

References

  1. ↑ Schnürch, Michael; Spina, Markus; Khan, Ather Farooq; Mihovilovic, Marko D.; Stanetty, Peter (2007). "Halogen dance reactions—A review". Chem. Soc. Rev. 36 (7): 1046–1057. doi:10.1039/B607701N.
  2. ↑ J. Fröhlich; C. Hametner. "First halogen dance reactions and their selective prevention on bromofurans". Institute of Organic Chemistry, Technical University of Vienna. Retrieved 8 October 2018.
  3. ↑ "Base catalysed halogen dance reactions". Institute of Organic Chemistry, Technical University of Vienna.
  4. ↑ James P. Stambuli; Nicolas Proust; Mathieu F. Chellat (2011). "Mechanistic Insight into the Halogen Dance Rearrangement of Iodooxazoles". Synthesis. 19: 3083–3088. doi:10.1055/s-0030-1260164.

General references

  • Participation of oligochlorobenzenes in the base-catalyzed halogen dance Martin H. Mach, Joseph F. Bunnett; J. Org. Chem.; 1980; 45(23); 4660-4666.
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