Tandem oxidation/halogenation of aryl allylic alcohols under Moffatt-Swern conditions |
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Authors: | Yin Jiandong Gallis Christina E Chisholm John D |
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Institution: | Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, New York 13244, USA. |
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Abstract: | Aryl allylic alcohols are converted to halogenated unsaturated ketones or allylic halides using excess Moffatt-Swern reagent. 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. The oxidation/halogenation reaction performs well with both oxalyl chloride and oxalyl bromide, providing access to the corresponding chlorides or bromides, respectively. |
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