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

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

Research output: Contribution to journalArticlepeer-review

22 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 languageEnglish (US)
Pages (from-to)7054-7057
Number of pages4
JournalJournal of Organic Chemistry
Volume72
Issue number18
DOIs
StatePublished - Aug 31 2007

ASJC Scopus subject areas

  • Organic Chemistry

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