A STUDY ON THE AMINOMERCURATION-NUCLEOPHILIC DEMERCURATION OF CIS-CIS-1,5-CYCLOOCTADIENE - STEREOSELECTIVE SYNTHESIS OF 2,6-DISUBSTITUTED-9-AZA BICYCLO[3.3.1]NONANES

被引：11

作者：

BARLUENGA, J ^{[1
]}

PEREZPRIETO, J ^{[1
]}

ASENSIO, G ^{[1
]}

GARCIAGRANDA, S ^{[1
]}

SALVADO, MA ^{[1
]}

机构：

[1] UNIV VALENCIA,FAC FARM,DEPT QUIM ORGAN,AVDA BLASCO IBANEZ 13,E-46010 VALENCIA,SPAIN

来源：

TETRAHEDRON | 1992年 / 48卷 / 18期

关键词：

AMINOMERCURATION NUCLEOPHILIC-DEMERCURATION; CIS-CIS-1,5-CYCLOOCTADIENE; STEREOSELECTIVE SYNTHESIS; 2,6-DISUBSTITUTED-9-AZABICYCLO-[3.3.1]NONANES; X-RAY STRUCTURE;

D O I：

10.1016/S0040-4020(01)92272-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The aminomercuration of cis-cis-1,5-Cyclooctadiene with a series of mercury(II) salts followed by nucleophilic displacement of mercury by aromatic amines, water and nitrate ion has been studied. As a result, bicyclic triamines, aminoalcohols and nitrate esters have been obtained respectively in clean processes which occur under total stereoelectronic control by involvement of a tricyclic aziridium ion to afford a single stereoisomer in each case, The influence of the counter ion and the basicity of the amine on the tandem aminomercuration-demercuration is discussed.

引用

页码：3813 / 3826

页数：14