Catalytic effects of hydrogen-bond acceptor solvent on nucleophilic aromatic substitution reactions in non-polar aprotic solvent: reactions of phenyl 2,4,6-trinitrophenyl ether with amines in benzene-acetonitrile mixtures

被引：26

作者：

Banjoko, O ^{[1
]}

Babatunde, IA ^{[1
]}

机构：

[1] Univ Lagos, Dept Chem, Lagos, Nigeria

来源：

TETRAHEDRON | 2005年 / 61卷 / 33期

关键词：

hydrogen-bond donor; hydrogen-bond acceptor; amineacetonitrile aggregate;

D O I：

10.1016/j.tet.2005.06.009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The effect of addition of small amounts of hydrogen-bond acceptor solvent, acetonitrile, to the benzene medium of the reactions of phenyl 2,4,6-trinitrophenyl ether with aniline and cyclohexylamine, respectively have been investigated. The addition produced similar effects in the two reactions-continuous rate increase with increasing amounts of acetonitrile. The results are interpreted in terms of the effect of amine-solvent interaction on the nucleophilicity of the amines and are in accord with our expectations based on the effects observed for hydrogen-bond donor solvent, methanol on the same reactions. It is also established from the results that the role of hydrogen-bond acceptor co-solvent could be played by an added more basic non-nucleophilic amine. (c) 2005 Published by Elsevier Ltd.

引用

收藏

页码：8035 / 8040

页数：6

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