Transhalogenation
Transhalogenation is a substitution reaction in which the halide of a halide compound is exchanged for another halide.[1]
Finkelstein reaction
A common method is halide metathesis. An example is the conversion of
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
As a halogen source for transhalogenation,
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
- Yoel Sasson (2009-12-15). "Formation of Carbon-Halogen Bonds (Cl, Br, I)". PATai's Chemistry of Functional Groups. Chichester, UK: John Wiley & Sons, Ltd. pp. pat0011. )
- "transhalogenation - Wiktionary". 27 October 2018.
References
- ISBN 9780470771723.
- ^ )
- ^ DE 68918542T, "Verfahren zur Transhalogenierung einer Halogenphosphor-Verbindung mit Fluorwasserstoff", published 1989-08-30
- )
- PMID 19480440
- )