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Synlett 2011(19): 2819-2822  
DOI: 10.1055/s-0031-1289860
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Unique Salt Effect on the High Yield Synthesis of Acid-Labile Terpene Oxides Using Hydrogen Peroxide under Acidic Aqueous Conditions

Houjin Hachiyaa, Yoshihiro Kon*a, Yutaka Onoa, Kiyoshi Takumib, Naoki Sasagawab, Yoichiro Ezakib, Kazuhiko Sato*a
a National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5 Higashi 1-1-1, Tsukuba, Ibaraki 305-8565, Japan
Fax: +81(29)8614670; e-Mail: y-kon@aist.go.jp;
b Arakawa Chemical Industries, Ltd., Tsukuba Okubo 5, Tsukuba, Ibaraki 300-33 Japan
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Publication History

Received 18 August 2011
Publication Date:
09 November 2011 (online)

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Abstract

Acid-labile epoxides such as α-pinene oxide are (effectively) synthesized in high yield from the epoxidation of terpenes with aqueous H2O2 catalyzed by Na2WO4, [Me(n-C8H17)3N]HSO4, and PhP(O)(OH)2 in the presence of Na2SO4 as an auxiliary additive under organic solvent-free conditions at ambient temperature. Origin of the salt effect is considered that the addition of a saturated amount of Na2SO4 to aqueous H2O2 strongly inhibited the undesired hydrolysis of the acid-labile epoxide products, despite the highly acidic reaction conditions.

Key words

oxidation - catalysis - epoxides - terpenoids - green chemistry

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