N-15 NUCLEAR-MAGNETIC-RESONANCE STUDIES OF AZABICYCLES - UNUSUAL DESHIELDING OF NITROGEN IN THE 7-AZABICYCLO[2.2.1]HEPTYL RING-SYSTEM

被引：15

作者：

BELKACEMI, D ^{[1
]}

DAVIES, JW ^{[1
]}

MALPASS, JR ^{[1
]}

NAYLOR, A ^{[1
]}

SMITH, CR ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1992年 / 48卷 / 46期

关键词：

N-15 NMR SPECTRA; BRIDGED BICYCLIC AMINES; 7-AZABENZONORBORNANES ENES; TROPANES ENES; HOMOTROPANES ENES; SLOW NITROGEN INVERSION;

D O I：

10.1016/S0040-4020(01)89045-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-15-enriched samples of derivatives of the 7-azabicyclo[2.2.1]heptyl system were synthesised and N-15 NMR spectra were recorded using N-15-enriched and natural abundance samples; separate signals were observed for the two invertomers in N-methyl and N-chloro derivatives. Considerable deshielding was observed in comparison with simple amines and with 8-azabicyclo[3.2.1]octyl and 9-azabicyclo[4.2.1]nonyl analogues. Predictable changes in chemical shift resulted from substitution at nitrogen and at alpha-carbons; the effects of configuration at nitrogen, of unsaturation, and of substitution further from the nitrogen were also explored.

引用

页码：10161 / 10176

页数：16

共 37 条

[1] A SIMPLE APPROACH TO NORTROPANE AND NORTROP-6-ENE DERIVATIVES [J].