Wurtz–Fittig reaction

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Wurtz–Fittig reaction
Named after Charles-Adolphe Wurtz
Wilhelm Rudolph Fittig
Reaction type Coupling reaction
Identifiers
Organic Chemistry Portal wurtz-fittig-reaction

The Wurtz–Fittig reaction is the chemical reaction of aryl halides with alkyl halides and sodium metal in the presence of dry ether to give substituted aromatic compounds.[1][2] The reaction is named after Charles-Adolphe Wurtz, who discovered in 1855 a similar reaction between two alkyl halides (Wurtz reaction), and Rudolph Fittig, who discovered that aryl halides also undergo this reaction.

The Wurtz–Fittig reaction

The reaction works best for forming asymmetrical products if the halide reactants are somehow separate in their relative chemical reactivities. One way to accomplish this is to form the reactants with halogens of different periods. Typically the alkyl halide is made more reactive than the aryl halide, increasing the probability that the alkyl halide will form the organosodium bond first and thus act more effectively as a nucleophile toward the aryl halide.[3] Typically the reaction is used for the alkylation of aryl halides; however, with the use of ultrasound the reaction can also be made useful for the production of biphenyl compounds.[4]

See also[edit]

References[edit]

  1. ^ Bernhard Tollens, Rudolph Fittig (1864). "Ueber die Synthese der Kohlenwasserstoffe der Benzolreihe". Annalen der Chemie und Pharmacie. 131 (3): 303–23. doi:10.1002/jlac.18641310307. 
  2. ^ Rudolph Fittig; Joseph König (1867). "Ueber das Aethyl- und Diäthylbenzol (p)". Annalen der Chemie und Pharmacie. 144 (3): 277–94. doi:10.1002/jlac.18671440308. 
  3. ^ Desai, K.R. (2008). Organic Name Reactions. Jaipur I India: Oxford Book Company. p. 259. ISBN 9788189473327. 
  4. ^ Laue, Thomas & Plagens, Andreas (2005). Named Organic Reactions 2nd Ed. Wolfsburg, Germany: John Wiely & Sons, Ltd. p. 305. ISBN 9780470010402.