Tandem oxidation/halogenation of aryl allylic alcohols under Moffatt-Swern conditions

Jiandong Yin; Christina E. Gallis; John D. Chisholm

doi:10.1021/jo0711992

Tandem oxidation/halogenation of aryl allylic alcohols under Moffatt-Swern conditions

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

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29 Scopus citations

Abstract

(Chemical Equation Presented) 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.

Original language	English (US)
Pages (from-to)	7054-7057
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	72
Issue number	18
DOIs	https://doi.org/10.1021/jo0711992
State	Published - Aug 31 2007

ASJC Scopus subject areas

Organic Chemistry

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abstract = "(Chemical Equation Presented) 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.",

author = "Jiandong Yin and Gallis, {Christina E.} and Chisholm, {John D.}",

year = "2007",

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journal = "Journal of Organic Chemistry",

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T1 - Tandem oxidation/halogenation of aryl allylic alcohols under Moffatt-Swern conditions

AU - Yin, Jiandong

AU - Gallis, Christina E.

AU - Chisholm, John D.

PY - 2007/8/31

Y1 - 2007/8/31

N2 - (Chemical Equation Presented) 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.

AB - (Chemical Equation Presented) 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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Tandem oxidation/halogenation of aryl allylic alcohols under Moffatt-Swern conditions

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