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Transhalogenation is a substitution reaction in which the
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. Transhalogenation has been described as a gentle method for the synthesis of fluoroorganylboranes. It is also possible to produce aryliodides from the corresponding aryl chlorides or aryl bromides.
One investigation showed a possibility to perform transhalogenation by means of genetically modified enzymes (haloalkanes dehalogenases, HLDs).
halide
In chemistry, a halide (rarely halogenide) is a binary chemical compound, of which one part is a halogen atom and the other part is an element or radical that is less electronegative (or more electropositive) than the halogen, to make a fluor ...
of a halide compound is exchanged for another halide.
Finkelstein reaction
A common method is halide metathesis. An example is the conversion ofalkyl chloride
An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound containing at least one covalently bonded atom of chlorine. The chloroalkane class (alkanes with one or more hydrogens substituted by chlor ...
into alkyl fluoride
Organofluorine chemistry describes the chemistry of the organofluorines, organic compounds that contain the carbon–fluorine bond. Organofluorine compounds find diverse applications ranging from oil and water repellents to pharmaceuticals, refri ...
:
:C3H5-Cl + NaF → R-F + NaCl
This kind of reaction is called Finkelstein reaction. 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.
Details and biological use
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. Transhalogenation has been described as a gentle method for the synthesis of fluoroorganylboranes. It is also possible to produce aryliodides from the corresponding aryl chlorides or aryl bromides.
One investigation showed a possibility to perform transhalogenation by means of genetically modified enzymes (haloalkanes dehalogenases, HLDs).
Literature
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