Transhalogenation
Transhalogenation is a substitution reaction in which the halide of a halide compound is exchanged for another halide.[1]
Finkelstein reaction
[edit | edit source]A common method is halide metathesis. An example is the conversion of alkyl chloride into alkyl fluoride:
- C3H5-Cl + NaF → R-F + NaCl
This kind of reaction is called Finkelstein reaction.[2] However, it is also possible, for example, to produce phosphorus fluoride compounds by transhalogenating chlorine, bromine or iodine bound to phosphorus with a metal fluoride.[3]
Details and biological use
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As a halogen source for transhalogenation, metal halides (such as sodium fluoride or lithium fluoride) are often used, but also the use of onium halides is possible.[2] Transhalogenation has been described as a gentle method for the synthesis of fluoroorganylboranes.[4] It is also possible to produce aryliodides from the corresponding aryl chlorides or aryl bromides.[5]
One investigation showed a possibility to perform transhalogenation by means of genetically modified enzymes (haloalkanes dehalogenases, HLDs).[6]
Literature
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References
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