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Tandem Oxidation/Halogenation of Aryl Allylic Alcohols under Moffatt-Swern Conditions

Jiandong Yin, Christina E. Gallis and John D. Chisholm*

*Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, New York 13244, Email: jdchishosyr.edu

J. Yin, C. E. Gallis, J. D. Chisholm, J. Org. Chem., 2007, 72, 7054-7057.

DOI: 10.1021/jo0711992 (free Supporting Information)


Abstract

Aryl allylic alcohols are converted to halogenated unsaturated ketones or allylic halides under Moffatt-Swern Conditions using excess DMSO and oxalyl chloride or oxalyl bromide. Electron-poor aromatic rings favor formation of the halogenated ketone, while electron-donating substituents in the ortho or para positions favor formation of the allylic halide.

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proposed mechanism



Key Words

Swern Oxidation, Vinyl Bromides, Vinyl Chlorides, Allyl Chlorides


ID: J42-Y2007-2900