Formation of isomeric 3-azabicyclo[3.3.1]nonanes in a reaction of 1-(2-hydroxyethoxy)-2,4-dinitrobenzene with sodium borohydride, formaldehyde, and methylamine

被引：2
|
作者：
Atroshchenko, YM [1 ]
Shakhkel'dyan, IE
Borbulevich, OY
Shchukin, AN
Antipin, MY
Khrustalev, VN
机构：
[1] LN Tolstoi Tula State Pedagog Univ, Tula 300026, Russia
[2] Russian Acad Sci, Nesmeyanov Inst Organoelemental Cpds, Moscow, Russia
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 41卷 / 11期
基金：
俄罗斯基础研究基金会;
关键词：
Sodium; Formaldehyde; Adduct; Anionic Hydride; Hydride;
D O I：
10.1007/s11178-006-0019-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Anionic hydride adduct of 1-(2-hydroxyethoxy)-2,4-dinitrobenzene was brought into a double Mannich condensation with formaldehyde and methylamine to furnish a mixture of isomeric 3-azabicyclo[3.3.1]nonanes: 3-methyl-6-(2-hydroxyethoxy)-1,5-dinitro-3-azabicyclo[3.3.1]non-6-ene and 3-methyl-6,6-ethylenedioay-1,7-dinitro3-azabicyclo[3.3.1]nonane. By means of NMR spectroscopy, X-ray diffraction analysis, and quantum chemistry (PM3) we demonstrated that the spirocyclic isomer had chair-chair conformation with diequatorial orientation of substituents in positions 3 and 7.
引用
收藏
页码：1683 / 1689
页数：7
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