How Does Nucleophilic Aromatic Substitution Really Proceed in Nitroarenes? Computational Prediction and Experimental Verification

被引：0

作者：

Blaziak, Kacper ^{[1
]}

Danikiewicz, Witold ^{[1
]}

Mąkosza, Mieczyslaw ^{[1
]}

机构：

[1] Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, Warsaw,01-224, Poland

来源：

Journal of the American Chemical Society | 2016年 / 138卷 / 23期

关键词：

Sulfur compounds;

D O I：

暂无

中图分类号：

学科分类号：

摘要：

The aim of this paper is to present a correct and complete mechanistic picture of nucleophilic substitution in nitroarenes based on the results obtained by theoretical calculations and experimental observations coming from numerous publications, reviews, and monographs. This work gives the theoretical background to the very well documented experimentally yet still ignored observations that the addition of nucleophiles to halo nitroarenes resulting in the formation of σH adducts, which under proper reaction conditions can be transformed into the product of the SNArH reaction, is faster than the competing process of addition to the carbon atom bearing a nucleofugal group (usually a halogen atom) resulting in the classic SNAr reaction. Only when the σH adduct cannot be transformed into the SNArH reaction product, SNAr reaction is observed. © 2016 American Chemical Society.

引用

页码：7276 / 7281