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Selective Rhenium-Catalyzed Oxidation of Secondary Alcohols with Methyl Sulfoxide in the Presence of Ethylene Glycol, a Convenient One-Pot Synthesis of Ketals

Jeffrey B. Arterburn and Marc C. Perry

*Department of Chemistry and Biochemistry MSC 3C, New Mexico State University, P.O. Box 30001, Las Cruces, New Mexico 88003, Email: jarterbunmsu.edu

J. B. Arterburn, M. C. Perry, Org. Lett., 1999, 1, 769-771.

DOI: 10.1021/ol990755e (free Supporting Information)



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Abstract

ReOCl3(PPh3)2 catalyzes a rapid oxidation of secondary alcohols by DMSO in the presence of ethylene glycol and refluxing toluene to provide the corresponding ketals in very good yields. Methyl sulfide and water as byproducts of the reaction are easily removed.

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Key Words

1,3-dioxolanes, oxidation of secondary alcohols, DMSO


ID: J54-Y1999