β-硅基砜中[1,4]碳-氧-硅介导的消除重排的苯基加速。O -硅基化肉桂醇的合成

S. Menichetti, C. Stirling
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引用次数: 2

摘要

当砜1生成的碳离子与羰基化合物反应时,碳到氧硅的快速迁移重排导致o-硅基化肉桂醇发生。与相应的未取代砜3的行为相比,相邻苯环在这一过程中的强制作用得到了证明。
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Phenyl group acceleration of [1,4] carbon-to-oxygen silicon-mediated elimination–rearrangement in β-silyl sulfones. Synthesis of O -silylated cinnamyl alcohols
A very fast [1,4] carbon-to-oxygen silicon migration-rearrangement leading to O-silylated cinnamyl alcohols occurs when the carbanion generated from sulfone 1 is reacted with carbonyl compounds. The mandatory role of the adjacent phenyl ring in this process is demonstrated when compared to the behaviour of the corresponding unsubstituted sulfone 3.
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