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Synfacts 2009(12): 1394-1394  
DOI: 10.1055/s-0029-1218176
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

NbCl5/NbBr5-Mediated Alkoxide Rearrangements to Allylic and Allenic Halides

Contributor(s): Paul Knochel, Andreas J. Wagner
P. C. Ravikumar, L. Yao, F. F. Fleming*
Duquesne University, Pittsburgh, USA
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Publication History

Publication Date:
20 November 2009 (online)

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Significance

The addition of NbCl5 or NbBr5 to various allylic or propargylic alkoxides directly gives rise to allylic or allenic halides in good yields. A formal 3,3-rearrangement between the alkoxide and a NbX bond is presumed. The reaction is ­applicable to a range of aliphatic and aromatic ­alcohols, aldehydes, and ketones.