The reactions of substituted phenoxides with carbon dioxide in N, N-dimethylformamide (DMF) were studied.
In the phenoxides containing a methyl-, amino-, hydroxyl-, or chlorine-substituent, the carboxyl groups were introduced into the
para-position as well as
ortho-position. This unusual Kolbe-Schmidt type reaction hardly occurred in
meta-substituted phenoxides.
In DMF, with the exception of
o- and
p-aminophenoxides, the carboxylation was effected under rather mild conditions. Phenol derivatives containing a nitro-, sulfo-, carbamoyl-, or carboxyl-group underwent such reaction with difficulty.
Though a hydroxy acid was obtained in a low yield from 8-hydroxyquinoline, β-naphthol and pyrroles were fully devoid of reactivity.
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