Inherent Reactivity of Spiro-Activated Electrophilic Cyclopropanes,Chemistry - A European Journal

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Inherent Reactivity of Spiro-Activated Electrophilic Cyclopropanes
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2021-09-27 , DOI: 10.1002/chem.202103027
Patrick M Jüstel ₁ , Alexandra Stan ₁ , Cedric D Pignot ₁ , Armin R Ofial ₁

Affiliation

Ring, ring! The reactivity of spiro-activated electrophilic cyclopropanes was studied by following the kinetics of their S_N2-type ring-opening reactions with thiophenolate ions in DMSO at 20 °C. The experimentally determined second-order rate constants (k₂) correlated linearly with Mayr nucleophilicities N, basicities (pK_aH), and Hammett substituent constants of the thiophenolates, but parabolic Hammett plots revealed variable electrophile-dependent effects on the stabilization of the transition states.

中文翻译：

螺环活化的亲电环丙烷的固有反应性

响铃，响铃！通过跟踪螺环活化的亲电环丙烷在 20 °C 的 DMSO 中与苯硫酚离子的 S _N 2 型开环反应的动力学，研究了螺环活化的亲电环丙烷的反应性。实验确定的二阶速率常数 ( k ₂ ) 与迈尔亲核性N 、碱度 (p K _aH ) 和苯硫酚盐的哈米特取代基常数线性相关，但抛物线哈米特图揭示了对转变稳定性的不同亲电子依赖性影响州。

更新日期：2021-11-17

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