Efficient Epoxidation of Alkenes with Aqueous Hydrogen Peroxide Catalyzed by Methyltrioxorhenium and 3-Cyanopyridine

Hans Adolfsson*, Christophe Copéret, Jay P. Chiang and Andrei K. Yudin

*Department of Chemistry and the Skaggs Institute of Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 90237, Email: hans.adolfssonumu.se

H. Adolfsson, C. Copéret, J. P. Chiang, A. K. Yudin, J. Org. Chem., 2000, 65, 8651-8658.

DOI: 10.1021/jo005623+

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Abstract

Methyltrioxorhenium (MTO) catalyzes an epoxidation of alkenes with 30% aqueous hydrogen peroxide. The addition of 1-10 mol % of 3-cyanopyridine increases the system's efficiency resulting in high isolated yields of the corresponding epoxides. Alkenes yielding epoxides more sensitive to nucleophilic ring opening require a mixture of 3-cyanopyridine and pyridine.

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Olefin Epoxidation with Bis(trimethylsilyl) Peroxide Catalyzed by Inorganic Oxorhenium Derivatives. Controlled Release of Hydrogen Peroxide

A. K. Yudin, J. P. Chiang, H. Adolfsson, C. Copéret, J. Org. Chem., 2001, 66, 4713-4718.

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Key Words

methyltrioxorhenium, hydrogen peroxide, epoxides

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ID: J42-Y2000