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Synfacts 2009(12): 1394-1394
DOI: 10.1055/s-0029-1218176
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
P. C. Ravikumar, L. Yao, F. F. Fleming*
Duquesne University, Pittsburgh, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
20. November 2009 (online)
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.