For faster navigation, this Iframe is preloading the Wikiwand page for Halogen dance rearrangement.

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.[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.
{{bottomLinkPreText}} {{bottomLinkText}}
Halogen dance rearrangement
Listen to this article

This browser is not supported by Wikiwand :(
Wikiwand requires a browser with modern capabilities in order to provide you with the best reading experience.
Please download and use one of the following browsers:

This article was just edited, click to reload
This article has been deleted on Wikipedia (Why?)

Back to homepage

Please click Add in the dialog above
Please click Allow in the top-left corner,
then click Install Now in the dialog
Please click Open in the download dialog,
then click Install
Please click the "Downloads" icon in the Safari toolbar, open the first download in the list,
then click Install
{{::$root.activation.text}}

Install Wikiwand

Install on Chrome Install on Firefox
Don't forget to rate us

Tell your friends about Wikiwand!

Gmail Facebook Twitter Link

Enjoying Wikiwand?

Tell your friends and spread the love:
Share on Gmail Share on Facebook Share on Twitter Share on Buffer

Our magic isn't perfect

You can help our automatic cover photo selection by reporting an unsuitable photo.

This photo is visually disturbing This photo is not a good choice

Thank you for helping!


Your input will affect cover photo selection, along with input from other users.

X

Get ready for Wikiwand 2.0 ๐ŸŽ‰! the new version arrives on September 1st! Don't want to wait?