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Halogen dance rearrangement
The halogen dance rearrangement is a organic reaction where a halogen substituent moves to a new position on a 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-trobromobenzene in liquid ammonia with the aniline/potassium base system. The intermediate in this reaction is a 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.
references
Participation of oligochlorobenzenes in the base-catalyzed halogen dance Martin H. Mach, Joseph F. Bunnett; J. Org. Chem.; 1980; 45(23); 4660-4666.
Last updated: 05-28-2005 19:13:46
10-26-2009 08:16:03
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The contents of this article is licensed from www.wikipedia.org under the GNU Free Documentation License. Click here to see the transparent copy and copyright details