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: jdchisho
syr.edu
J. Yin, C. E. Gallis, J. D. Chisholm, J. Org. Chem., 2007, 72, 7054-7057.
DOI: 10.1021/jo0711992
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.
see article for more examples
proposed mechanism
Key Words
Swern Oxidation, Vinyl Bromides, Vinyl Chlorides, Allyl Chlorides
ID: J42-Y2007-2900
