Synthesis of Epoxides Catalyzed by a Halide-Free Reaction-Controlled Phase-Transfer Catalytic System: [(CH3(CH2)17)2N(CH3)2]3[PW4O32]/H2O2/Dioxan/Olefin

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doi:10.1071/CH08547

Synthesis of Epoxides Catalyzed by a Halide-Free Reaction-Controlled Phase-Transfer Catalytic System: [(CH₃(CH₂)₁₇)₂N(CH₃)₂]₃[PW₄O₃₂]/H₂O₂/Dioxan/Olefin

Yong Ding ^A ^B, Baochun Ma ^A, Dejie Tong ^A, Hui Hua ^A, Wei Zhao ^A

^A State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
^B Corresponding author. Email: dingyong1@lzu.edu.cn





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Australian Journal of Chemistry 62(7) 739–746 http://dx.doi.org/10.1071/CH08547
Submitted: 15 December 2008 Accepted: 15 April 2009 Published online: 13 July 2009

Abstract

The epoxidation of alkenes was successfully catalyzed by a recyclable catalytic system: [(CH₃(CH₂)₁₇)₂N(CH₃)₂]₃[PW₄O₃₂]/H₂O₂/dioxan/olefin. This new catalytic system is not only capable of catalyzing homogeneous epoxidation of alkenes with a unique reaction-controlled phase-transfer character, but also avoids the use of chlorinated solvents. The reactions were conducted in a biphasic mixture of aqueous H₂O₂/dioxan, and many kinds of alkenes could be efficiently converted to the corresponding epoxides in high yields. Both new and used [(CH₃(CH₂)₁₇)₂N(CH₃)₂]₃[PW₄O₃₂] catalyst was characterized by ³¹P magic angle spin NMR, and IR.