1,2,4-Trioxane versus 1,2-dioxolane formation in the mercury(II) acetate-mediated cyclisation of hemiperoxyacetals derived from allylic hydroperoxides

Abstract

Upon treatment with mercury(II) acetate and perchloric acid catalyst, hemiperoxyacetals derived from 1-phenlprop-2-enyl hydroperoxide afford 3,5,6-trisubstituted 1,2,4-trioxanes with high diastereoselectivity whereas those derived from 3-phenylprop-2-enyl hydroperoxide yield only 3-phenyl-4-mercurio-1,2-dioxolane.