Lu X, Zhang C, Xu Z
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Acc Chem Res. 2001 Jul;34(7):535-44. doi: 10.1021/ar000253x.
The development of some new synthetic reactions derived from nucleophilic addition of phosphines to electron-deficient carbon-carbon triple bonds is described. These reactions show that the phosphine plays the role of a nucleophile as well as an excellent leaving group. The central problem is to generate a 1,3-dipole from alkynoates or allenoates (2,3-butadienoates) by interaction with various phosphines. This study illuminates the unusual phenomena and shows how this understanding allows control of the reaction.
描述了一些由膦对缺电子碳 - 碳三键进行亲核加成衍生出的新型合成反应。这些反应表明膦既起到亲核试剂的作用，又作为优良的离去基团。核心问题是通过与各种膦相互作用，从炔酸酯或丙二烯酸酯（2,3 - 丁二烯酸酯）生成1,3 - 偶极子。这项研究阐明了这些异常现象，并展示了这种认识如何实现对反应的控制。
