Direct observation of the intermediate in vicarious nucleophilic substitutions of hydrogen

被引：36

作者：

Lemek, T

Makosza, M

Stephenson, DS

Mayr, H

机构：

[1] Univ Munich, Dept Chem, D-81377 Munich, Germany

[2] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 24期

关键词：

aromatic substitution; carbanions; elimination; kinetics; nucleophilic substitution;

D O I：

10.1002/anie.200351352

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Mononitrobenzene derivatives and 1-chloro-1-arylsulfonyl-methyl anions react with formation of stable σH adducts (see scheme; Ts = tosyl) which are observed by UV/Vis and NMR spectroscopy. The generally accepted energy profiles for vicarious nucleophilic substitutions with σH adducts as high-energy intermediates have to be revised.

引用

页码：2793 / 2795

页数：3

共 23 条

[1]

[Anonymous], 1991, NUCLEOPHILIC AROMATI

[2]

CHUPAKIN ON, 1994, NUCLEOPHILIC AROMATI

[3]

Donskaya O. V., 2002, Chem. Het. Comp, V38, P371, DOI DOI 10.1023/A:1016005818010

[4]

Donskaya OV, 2002, KHIM GETEROTSIKL+, P435