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; Baochun Ma; Dejie Tong; Hui Hua; Wei Zhao

doi:10.1071/CH08547

RESEARCH ARTICLE

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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 and Wei Zhao ^A

+ Author Affiliations

- Author Affiliations

^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

Australian Journal of Chemistry 62(7) 739-746 https://doi.org/10.1071/CH08547
Submitted: 15 December 2008 Accepted: 15 April 2009 Published: 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.

Acknowledgements

The present work was supported by the National Natural Science Foundation of China (grants no. 20702021 and 20803032). We gratefully thank Professor W. Wang for the measurement of solid-state NMR.

References

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

Abstract

Acknowledgements

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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