In the equimolar reaction of acrylonitrile with hydrogen peroxide to 2,3-epoxypropanamide (glycidamide), the selectivity and the yield of the epoxide were improved by adding aq. NaOH solution continuously at a constant rate. The conventional literature procedure, by controlled pH from 7.0 to 7.5, resulted in an unfavorable decomposition of hydrogen peroxide. 2,3-Epoxypropanamide could be easily converted to 2,3-dihydroxypropanamide (glyceramide) by a catalytic amount of commercially available acidic resins.
The reaction behavior of propylene oxide with boron trifluoride was affected remarkably by solvent. In dioxane, the isomerization to propionaldehyde proceeded smoothly and selectively, while the reaction behavior in heptane, benzene, and tetrahydrofuran was quite different from that in dioxane.
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