The Appel reaction uses a carbon tetrahalomethane and triphenylphosphine to convert a primary or secondary alcohol to an alkyl halide. First triphenylphosphine forms a phosphonium ion by abstracting a halogen from carbon tetrahalomethane. The alcohol then attacks the phosphonium ion, generating an oxyphosphonium intermediate. An SN2 displacement by the halide ion produces triphenylphosphine oxide and the alkyl halide. Inversion of configuration occurs if the carbon is asymmetric.

  • Reagents: Triphenyl Phosphine, Tetrahalomethane
  • Reactant: Primary or Secondary Alcohol
  • Product: Alkyl Halide
  • Type of Reaction: SN2


Top Citations

Original Paper

Related Reactions

  • Mitsunobu Reaction
  • Staudinger Reaction
  • Synthesis of Alkyl Bromides
  • Synthesis of Alkyl Chlorides
  • Dakin-West Reaction

Related Compounds

  • Triphenyl Phosphine (CAS 603-35-0)
  • Carbon Tetrachloride (CAS 56-23-5)
  • Carbon Tetraiodide (CAS 507-25-5)
  • Methyl Iodide (CAS 74-88-4)
  • Bromine (CAS 7726-95-6)
  • Iodine (CAS 7553-56-2)
By shuhan yang


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