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NbCl5/NbBr5-Mediated Alkoxide Rearrangements to Allylic and Allenic Halides
P. C. Ravikumar, L. Yao, F. F. Fleming*
Duquesne University, Pittsburgh, USA
20 November 2009 (online)
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.