Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 19, Pages 7294-7299Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo901287f
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Funding
- National Institutes of Health [2R15A1051352-03]
- National Science Foundation [CHE 0808996, 0421252 HRMS, 024872, 0614785]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0614785] Funding Source: National Science Foundation
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Addition of NbCl5 or NbBr5 to a series of magnesium, lithium, or potassium allylic or propargylic alkoxides directly provides allylic or allenic halides. Halogenation formally occurs through a metallahalo-[3,3] rearrangement, although concerted, ionic, and direct displacement mechanisms appear to operate competitively. Transposition of the olefin is equally effective for allylic alkoxides prepared by nucleophilic addition, deprotonation, or reduction. Experimentally, the niobium pentahalide halogenations are rapid, afford essentially pure (E)-allylic or -allenic halides after extraction, and are applicable to a range of aliphatic and aromatic alcohols, aldehydes, and ketones.
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