Balz–Schiemann reaction

Balz-Schiemann reaction
Named after Günther Balz
Günther Schiemann
Reaction type Substitution reaction
Identifiers
Organic Chemistry Portal balz-schiemann-reaction
RSC ontology ID RXNO:0000127

The Schiemann reaction (also called the Balz–Schiemann reaction) is a chemical reaction in which anilines (1) are transformed to aryl fluorides (3) via diazonium fluoroborates (2).[1][2] Named after the German chemists Günther Schiemann and Günther Balz, this reaction is the preferred route to fluorobenzene and some related derivatives,[3] including 4-fluorobenzoic acid.[4]

The reaction is similar to the Sandmeyer reaction, which converts diazonium salts to other aryl halides.[5]

References

  1. ↑ Günther Balz, Günther Schiemann (1927). "Über aromatische Fluorverbindungen, I.: Ein neues Verfahren zu ihrer Darstellung". Ber. 5 (60): 1186–1190. doi:10.1002/cber.19270600539.
  2. ↑ Roe, A. Org. React. 1949, 5, 193. (Review)
  3. ↑ Flood, D. T. (1943). "Fluorobenzene". Org. Synth.; Coll. Vol. 2, p. 295
  4. ↑ G. Schiemann; W. Winkelmüller (1943). "p-Fluorobenzoic Acid". Org. Synth.; Coll. Vol. 2, p. 299
  5. ↑ Swain, C. G.; Rogers, R. J. (1975). "Mechanism of formation of aryl fluorides from arenediazonium fluoborates". J. Am. Chem. Soc. 97: 799–800. doi:10.1021/ja00837a019.
This article is issued from Wikipedia - version of the Monday, September 28, 2015. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.