ISSN:
0009-2940
Keywords:
Doak phosphonylation
;
Phase-transfer catalysts
;
Phosphonic acid, derivatives
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Preparation of Unsubstituted and Chlorine-Carrying [(Trifluoromethyl)phenyl]phosphonic Acids by a Modified Doak-Freedman ProcedureThe performance of cuprous chloride and different phase-transfer catalysts using the Doak-Freedman procedure for preparing aromatic phosphonic acids have been compared by measurements of the evolved nitrogen volume in an eudiometer tube. In the investigated cases CuCl could well be exchanged by phase-transfer catalysts. With the new method the already known [3-(trifluoromethyl)phenyl]phosphonic acid, and the new [2-chloro-5-(trifluoromethyl)phenyl]phosphonic acid, [4-chloro-3-(trifluoromethyl)phenyl]phosphonic acid, as well as [2,4-dichloro-5-(trifluoromethyl)phenyl]phosphonic acid were prepared. The good solubility of the phase-transfer catalysts in water facilitates the separation of the catalysts from the reaction product, a property not observed for the copper compound. Other phosphonic acids may be prepared as well.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19891221032
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