NUCLEOPHILIC-SUBSTITUTION REACTIONS OF ISOPROPYL BENZENESULFONATES WITH ANILINES AND BENZYLAMINES

被引：10

作者：

OH, HK ^{[1
]}

KWON, YB ^{[1
]}

LEE, I ^{[1
]}

机构：

[1] INHA UNIV,DEPT CHEM,INCHON 402751,SOUTH KOREA

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 1993年 / 6卷 / 06期

关键词：

D O I：

10.1002/poc.610060607

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The nucleophilic substitution reactions of isopropyl arenesulphonates with anilines and benzylamines in acetonitrile at 65.0-degrees-C were investigated. The cross-interaction constants rho(XZ) (and beta(XZ)) between substituents in the nucleophile (X) and leaving group (Z) are positive and relatively small. The transition state (TS) variation is consistent with that predicted by the More O'Ferrall-Jencks diagram, as expected from the positive rho(XZ). The small magnitude of rho(XZ) correctly reflects a relatively loose TS structure, in contrast to the tight TS for ethyl (or methyl) derivatives under similar reaction conditions.

引用

页码：357 / 360

页数：4

共 25 条

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