Cross-linked anion exchange latexes 20, 150, and 1200 nm in diameter were p
repared via microemulsion, emulsion, and dispersion copolymerization, respe
ctively, of vinylbenzyl chloride, styrene, and divinylbenzene followed by t
reatment with trimethylamine or tributylamine. As catalysts for the unimole
cular decarboxylation of 6-nitrobenzisoxazole-1-carboxylate (1) the tributy
lammonium ion latexes were much more active than the trimethylammonium ion
latexes. There were only small differences in the rates of decarboxylation
in the three different tributylammonium ion latexes, and first-order kineti
cs were found at all relative concentrations of ion exchange sites and 1 in
the 20 and 150 nm particle dispersions. Retardation of the rate both early
and late in the reaction using a low concentration of the 1200 nm particle
s is attributed to slow mass transfer of 1 from solution to the particle su
rface and to competitive inhibition by the product ion.