Browse Nearby Entries
Hofmann rearrangement
1 reference results for: Hofmann rearrangement
Wikipedia
The Hofmann rearrangement is the organic reaction of a primary amide to a primary amine with one fewer carbon atom.
The reaction of bromine with sodium hydroxide forms sodium hypobromite in situ, which transforms the primary amide into an intermediate isocyanate. The intermediate isocyanate is hydrolyzed to a primary amine giving off carbon dioxide.
The reaction is named after its discoverer: August Wilhelm von Hofmann. This reaction is also sometimes called the Hofmann degradation, and should not be confused with the Hofmann elimination.
Variations
Several reagents can substitute for bromine. N-Bromosuccinimide and [[1,8-Diazabicycloundec-7-ene|1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)]] can effect a Hofmann rearrangement. In the following example, the intermediate isocyanate is trapped by methanol forming a carbamate.A mild alternative to bromine is also (bis(trifluoroacetoxy)iodo)benzene.
References
See also
- Beckmann rearrangement
- Curtius rearrangement
- Iodoform reaction
- Lossen rearrangement
- Schmidt reaction
- Weerman degradation
Wikipedia, the free encyclopedia © 2001-2006 Wikipedia contributors (Disclaimer)
This article is licensed under the GNU Free Documentation License.
Last updated on Wednesday June 25, 2008 at 08:33:53 PDT (GMT -0700)
View this article at Wikipedia.org - Edit this article at Wikipedia.org - Donate to the Wikimedia Foundation
This article is licensed under the GNU Free Documentation License.
Last updated on Wednesday June 25, 2008 at 08:33:53 PDT (GMT -0700)
View this article at Wikipedia.org - Edit this article at Wikipedia.org - Donate to the Wikimedia Foundation
Share This:
Copyright © 2008, Dictionary.com, LLC. All rights reserved.