Transhalogenation

Source: Wikipedia, the free encyclopedia.

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

An enzyme-catalyzed transhalogenation.

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.
    ISBN 978-0-470-68253-1. {{cite book}}: |periodical= ignored (help
    )
  • "transhalogenation - Wiktionary". 27 October 2018.

References

  1. .
  2. ^
    ISBN 978-0-470-68253-1. {{cite book}}: |periodical= ignored (help
    )
  3. ^ DE 68918542T, "Verfahren zur Transhalogenierung einer Halogenphosphor-Verbindung mit Fluorwasserstoff", published 1989-08-30 
  4. ISSN 0022-328X{{citation}}: CS1 maint: multiple names: authors list (link
    )
  5. ISSN 1615-4150{{citation}}: CS1 maint: multiple names: authors list (link
    )