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The fluorous Swern and Corey-Kim reaction: scope and mechanism

David Crich* and Santosh Neelamkavil

*Departement of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607-7061, USA, Email:

D. Crich, S. Neelamkavil, Tetrahedron, 2002, 58, 3865-3870.

DOI: 10.1016/S0040-4020(02)00207-7

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Fluorous sulfides and sulfoxides are effective odor-free reagents for the Corey-Kim and Swern oxidations of diversely functionalized primary and secondary alcohols to aldehydes and ketones. The reagents can be recovered in high yield by a continuous fluorous extraction of the reaction mixture.

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Key Words

Oxidation, Ylids, Sulfoxides, Fluorine and Compounds, Swern Oxidation, Corey-Kim Oxidation, Aldehydes, Ketones

ID: J72-Y2002-100