Liquid-Phase Decarboxylation of Aromatic Haloformates:  A New Access to Chloro- and Fluoroaromatics

The treatment of phenyl chloroformates 1 with a Lewis acid in the liquid phase resulted in decarboxylation to the corresponding chloroaromatics 2. Fluoroaromatic compounds were synthesized from phenylchloroformates 1 through a sequential fluorination/decarboxylation in the liquid phase by treatment...

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Bibliographic Details
Published in:Journal of organic chemistry 1998-04, Vol.63 (8), p.2493-2496
Main Authors: Lui, Norbert, Marhold, Albrecht, Rock, Michael H
Format: Article
Language:English
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Summary:The treatment of phenyl chloroformates 1 with a Lewis acid in the liquid phase resulted in decarboxylation to the corresponding chloroaromatics 2. Fluoroaromatic compounds were synthesized from phenylchloroformates 1 through a sequential fluorination/decarboxylation in the liquid phase by treatment with excess anhydrous hydrogen fluoride under mild conditions. In all cases, yields were increased by performing the reaction in 1,2,4-trichlorobenzene, which is inert to Friedel−Crafts reactions.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9716486