Phosphonium Phenolate Zwitterion
<i>vs</i>
Phosphonium Ylide: Synthesis, Characterization and Reactivity Study of a Trimethylphosphonium Phenolate Zwitterion
作者:Jing Xiao、Qiang Li、Ruwei Shen、Shigeru Shimada、Li‐Biao Han
DOI:10.1002/adsc.201901303
日期:2019.12.17
CD3CN with substrates bearing weakly acidic hydrogens. It exhibits similar reactivity to phosphorus ylides for olefinations of aldehydes. A possible tautomerization between the phosphonium phenolate zwitterion and phosphonium ylide is proposed for the first time to rationalize the unique reactivity.
4-对甲氧基-3-(三甲基膦酸)酚盐是从PMe 3的区域选择性加成到对苯二酚单缩醛中获得的。该化合物与D 2 O或CD 3 CN进行氢同位素交换,并且能够催化CD 3 CN与带有弱酸性氢的底物进行H / D交换。它对醛的烯化具有与磷酰磷相似的反应性。首次提出了酚盐两性离子与叶立德lide之间可能的互变异构,以合理化独特的反应性。