Unique Salt Effect on Highly Selective Synthesis of Acid-Labile Terpene and Styrene Oxides with a Tungsten/H₂O₂ Catalytic System under Acidic Aqueous Conditions

Abstract

Acid-labile epoxides such as terpene and styrene oxides are effectively synthesized in high yields with good selectivities using tungsten-catalyzed hydrogen peroxide epoxidation in the presence of Na₂SO₄. The salt effect is thought to originate with the addition of a saturated amount of Na₂SO₄ to aqueous H₂O₂; this addition strongly inhibited the undesired hydrolysis of the acid-labile epoxy products, despite the biphasic conditions of substrate as oil phase and H₂O₂ as acidic aqueous phase.

Key words

oxidation - catalysis - epoxides - terpenoids - green chemistry

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