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Synthesis 2011(7): 1092-1098  
DOI: 10.1055/s-0030-1258467
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Effective Synthesis of Acid-Sensitive Epoxides via Oxidation of Terpenes and Styrenes Using Hydrogen Peroxide under Organic Solvent-Free Conditions

Yoshihiro Kon, Houjin Hachiya, Yutaka Ono, Tomohiro Matsumoto, Kazuhiko Sato*
National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5 Higashi 1-1-1, Tsukuba, Ibaraki 305-8565, Japan
Fax: +81(29)8614578; e-Mail: k.sato@aist.go.jp;
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Publication History

Received 16 December 2010
Publication Date:
10 March 2011 (online)

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Abstract

An efficient epoxidation process for various terpenes and styrenes using a hydrogen peroxide-tungsten catalytic system with organic solvent- and halide-free conditions was developed. In the presence of the catalytic system, Na2WO4, PhP(O)(OH)2, and [Me(n-C8H17)3N]HSO4, and under weak acidic conditions, hydrogen peroxide successfully epoxidized α-pinene to α-pinene oxide in 95% selectivity at 91% conversion, while the previously published conditions utilizing NH2CH2P(O)(OH)2 as a promoter provided no epoxide.

Key words

oxidation - catalysis - epoxides - terpenoids - styrenes

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