Allylic and allenic halide synthesis via NbCl5-and NbBr5-mediated alkoxide rearrangements

PC Ravikumar, L Yao, FF Fleming

Index: Ravikumar; Yao, Lihua; Fleming, Fraser F. Journal of Organic Chemistry, 2009 , vol. 74, # 19 p. 7294 - 7299

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Citation Number: 18

Abstract

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 metalla-halo-[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 ...