Abstract
AbstractCis‐ and trans‐2,5‐diallyloxy‐2,5‐dihydrofuran have been prepared by acid catalyzed transacetalization of 2,5‐dimethoxy‐2,5‐dihydrofuran with allyl alcohol. As a by‐product, 1,1,3‐triallyloxypropane was formed from 2‐allyloxy‐2,5‐dihydrofuran intermediates. The cis/trans configuration has been determined by NMR (chiral lanthanide shift reagent) and MS (elimination of allyl alcohol). Oxidation of the cis and trans compounds by potassium permanganate yielded meso‐ and (±)‐2,2′‐bis(carboxymethoxy)oxydiacetic acid, respectively. The calcium sequestering properties of the latter compounds were superior to those of the acetal polycarboxylate obtained by sucrose oxidation. This is due to the extra steric hindrance encountered for the latter upon calcium complexation.
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