ELECTRONIC CONTROL OF STEREOSELECTIVITY IN THE CHLORINATION OF 1,4-DIHYDRO-1,4-IMINONAPHTHALENES (7-AZABENZONORBORNADIENES) WITH N-CHLOROSUCCINIMIDE

被引：25

作者：

DAVIES, JW ^{[1
]}

DURRANT, ML ^{[1
]}

WALKER, MP ^{[1
]}

MALPASS, JR ^{[1
]}

机构：

[1] UNIV LEICESTER,DEPT CHEM,LEICESTER LE1 7RH,ENGLAND

来源：

TETRAHEDRON | 1992年 / 48卷 / 21期

关键词：

7-AZABENZONORBORNYL DERIVATIVES; N-CHLOROAMINES; STEREOELECTRONIC CONTROL; SLOW NITROGEN INVERSION; INVERSION BARRIERS; INVERTOMER PREFERENCES;

D O I：

10.1016/S0040-4020(01)80447-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chlorination of a range of secondary amines based on the 1,4-dihydro-1,4-iminonaphthalene (7-azabenzonorbornadiene) ring system is described. At low temperatures, the ratio of syn- and anti- N-chloroamines formed under conditions of kinetic control can be determined; this ratio is shown to be influenced substantially by variation in the electronic character of the aryl ring. At higher temperatures, inversion at nitrogen leads to different (thermodynamic) invertomer ratios which also vary as a function of substitution. Substituents in the aryl ring and in the bicyclic skeleton also influence the nitrogen inversion barrier.

引用

收藏

页码：4379 / 4398

页数：20

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