Unequivocal experimental evidence for a unified lithium salt-free Wittig reaction mechanism for all phosphonium ylide types: reactions with β-heteroatom-substituted …

PA Byrne, DG Gilheany

文献索引：Byrne, Peter A.; Gilheany, Declan G. Journal of the American Chemical Society, 2012 , vol. 134, # 22 p. 9225 - 9239

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被引用次数: 45

摘要

The true course of the lithium salt-free Wittig reaction has long been a contentious issue in organic chemistry. Herein we report an experimental effect that is common to the Wittig reactions of all of the three major phosphonium ylide classes (non-stabilized, semi- stabilized, and stabilized): there is consistently increased selectivity for cis-oxaphosphetane and its derived products (Z-alkene and erythro-β-hydroxyphosphonium salt) in reactions ...