A new procedure for olefin oxiranation by peroxybenzimidic acid; synthesis of some carbohydrate-precursor oxirans and other epoxides

Abstract

Synthesis of cis- and trans-2-methoxy-3,4-epoxytetrahydropyrans (4) and (5), 3,4-anhydro-1,2-isopropylidene-β-DL-arabinopyranose (6), and the cis- and trans-2-methoxy-3,4-epoxytetrahydrofurans (7) and (S), which are carbohydrate-precursor oxirans, using a new procedure of oxiranation with peroxybenzimidic acid and potassium carbonate as the basic catalyst is described. The method has been extended to the oxiranation of several olefins such as indene (9), oct-1-ene (10), trans-β-methylstyrene (11), allyl alcohol (12), and chroman-4-one (13). In all cases, the method appears to be efficient and produces the oxirans in excellent yields after short reaction times.