Wurtz–Fittig reaction

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The Wurtz–Fittig reaction is the chemical reaction of aryl halides with alkyl halides and sodium metal 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 also aryl halides 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 of type Ph–Ph.[4]

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; and Plagens, Andreas (2005). Named Organic Reactions 2nd Ed. Wolfsburg, Germany: John Wiely & Sons, Ltd. p. 305. ISBN 9780470010402. 

See also[edit]