ACIDITY OF HYDROCARBONS .27. PROTON EXCHANGE RATES OF FLUOROBENZENE WITH LITHIUM CYCLOHEXYLAMIDE

被引：42

作者：

STREITWIESER, A

MARES, F

机构：

[1] Department of Chemistry, University of California, Berkeley

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1968年 / 90卷 / 03期

关键词：

D O I：

10.1021/ja01005a016

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Deuterium and tritium exchange in aryl positions of fluorobenzene and benzotrifluoride were studied with lithium cyclohexylamide in cyclohexylamine at 25°. Rates for D and T exchange relative to benzene are: fluorobenzene –2, 6.3 × 105, 3.4 × 105; –3,107,86; –4,11.2, 9.1; benzotrifluoride –3, 580, 390. These rates are in only qualitative agreement with previous work and are interpreted with a field effect model for inductive effects. 2,5-Difluorotoluene-α-d is found to exchange 350 times faster than toluene-α-d. © 1968, American Chemical Society. All rights reserved.

引用

页码：644 / +

页数：1

共 21 条

[1] ELECTROPHILIC SUBSTITUTION AT SATURATED CARBON .14. ASYMMETRIC SOLVATION OF CARBANIONS IN STEREOSPECIFIC HYDROGEN-DEUTERIUM EXCHANGE REACTIONS [J].