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Halogen dance rearrangement



The halogen dance rearrangement is an organic reaction in which a halogen substituent moves to a new position on an aromatic ring system. 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 [1] and thiophene [2] compounds.

Additional recommended knowledge

References

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

 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Halogen_dance_rearrangement". A list of authors is available in Wikipedia.
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