通过铌卤化物[3,3]重排将醛和酮直接转化为烯丙基卤化物
Direct Conversion of Aldehydes and Ketones to Allylic Halides by a NbX(5-)[3,3] Rearrangement.
作者信息
Fleming Fraser F, Ravikumar P C, Yao Lihua
机构信息
Department of Chemistry and Biochemistry, Duquesne University, Pittsburgh, Pennsylvania 15282-1530.
出版信息
Synlett. 2009;2009(7):1077-1080. doi: 10.1055/s-0028-1088222.
Abstract
Sequential addition of vinylmagnesium bromide and NbCl(5), or NbBr(5), to a series of aldehydes and ketones directly provides homologated, allylic halides. Transposition of the intermediate vinyl alkoxide is envisaged through a metalla-halo-[3,3] rearrangement with concomitant delivery of the halogen to the terminal carbon. The [3,3] rearrangement is equally effective for the conversion of a propargyllic alcohol to the corresponding allenyl bromide.
摘要
向一系列醛和酮中依次加入乙烯基溴化镁和五氯化铌或五溴化铌，可直接得到同系的烯丙基卤化物。中间体乙烯醇盐的重排被设想为通过金属-卤代-[3,3]重排，同时将卤素传递到末端碳上。[3,3]重排对于将炔丙醇转化为相应的烯丙基溴同样有效。
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引用本文的文献
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Allylic and allenic halide synthesis via NbCl(5)- and NbBr(5)-mediated alkoxide rearrangements.通过五氯化铌和五溴化铌介导的醇盐重排合成烯丙基卤化物和联烯基卤化物
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