MECHANISMS OF AROMATIC NUCLEOPHILIC-SUBSTITUTION REACTIONS IN ETHYL-ACETATE AND TETRAHYDROFURAN

被引：12

作者：

AKINYELE, ET ^{[1
]}

ONYIDO, I ^{[1
]}

HIRST, J ^{[1
]}

机构：

[1] QUEENS UNIV,DEPT CHEM,KINGSTON K7L 3N6,ONTARIO,CANADA

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 1990年 / 3卷 / 01期

关键词：

D O I：

10.1002/poc.610030109

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The kinetics of the reactions of 1‐chloro‐, 1‐fluoro‐ and 1‐phenoxy‐2,4‐dinitrobenzene with piperidine, n‐butylamine and benzylamine, and in the case of the ether, morpholine were studied as functions of nucleophile, DABCO and pyridine concentrations in tetrahydrofuran and ethyl acetate. The reactions of the ether with n‐butylamine and benzylamine in benzene were also studied as functions of nucleophile, DABCO and pyridine concentrations. A comparison with results in the literature indicated that the reactions in tetrahydrofuran and ethyl acetate resemble those in dipolar aprotic solvents when primary amines are the nucleophiles and those in aprotic solvents when the nucleophile is a secondary amine. An explanation is suggested for the observation that whereas the reactions of 1‐phenoxy‐2,4‐dinitrobenzene with piperidine and morpholine in both tetrahydrofuran and ethyl acetate are strongly catalysed by the nucleophiles, they are not catalysed by pyridine and there is either extremely weak or no catalysis by DABCO. Copyright © 1990 John Wiley & Sons Ltd.

引用

页码：41 / 47

页数：7

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