Studies on the deprotonation and subsequent [1,4]-Wittig rearrangement of α-benzyloxyallylsilanes |
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Authors: | Edith N. Onyeozili |
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Affiliation: | Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA |
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Abstract: | Upon exposure to s-BuLi, benzyloxyallylsilane undergoes an unusually rapid and efficient [1,4]-Wittig rearrangement. Herein we describe efforts aimed at trapping the intermediate α-carbanion with an electrophile prior to rearrangement. The results of these experiments indicate that α-deprotonation and bond reorganization are separate events. Findings herein further indicate that the future success of benzyloxyallylsilanes in [1,4]-Wittig rearrangements will likely hinge on the acidity of the benzylic protons. |
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Keywords: | [1,4]-Wittig rearrangement Deprotonation Organosilanes Carbanion |
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