Three‐phase carboxylation reactions of poly(chloromethylstyrene) beads with sodium nitrite

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<jats:title>Abstract</jats:title><jats:p>The formation of carboxylic acid groups (carboxyl + ester groups) was found in a threephase reaction of crosslinked poly(chloromethylstyrene) beads with an excess amount of sodium nitrite in immiscible solvents of benzene and water with tetrabutylammonium bromide as a phase transfer catalyst (PTC), and the dependence of carboxylic acid yield on the experimental conditions was studied. The product contains hydroxyl groups and ester bonds besides carboxyl groups. It was tentatively considered that the carboxyl groups are produced by direct oxidation of chloromethylstyrene groups by nitrous anions. Nitrous anions do not only act as a nucleophile but also as an oxidative reagent in this case.</jats:p>

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