Urotropine Isomer (1,4,6,10-Tetraazaadamantane): Synthesis, Structure, and Chemistry

被引：15

作者：

Semakin, Artem N. ^{[1
]}

Sukhorukov, Alexey Yu ^{[1
]}

Nelyubina, Yulia V. ^{[2
]}

Khomutova, Yulia A. ^{[1
]}

Ioffe, Sema L. ^{[1
]}

Tartakovsky, Vladimir A. ^{[1
]}

机构：

[1] ND Zelinskii Inst Organ Chem, Moscow 119991, Russia

[2] AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 13期

基金：

俄罗斯基础研究基金会; 俄罗斯科学基金会;

关键词：

TRANSITION-METAL-COMPLEXES; CRYSTAL-STRUCTURE; ADAMANTANE; HEXAMETHYLENETETRAMINE; SCAFFOLDS;

D O I：

10.1021/jo5007703

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first synthesis of 1,4,6,10-tetraazaadamantane, the C-3v-symmetrical structural isomer of urotropine (1,3,5,7-tetraazaadamantane), and a series of its derivatives is reported. X-ray and quantum-chemical studies revealed remarkable distinctions in structures of urotropine and "isourotropine" cations, probably arising from different types of hyperconjugation between lone electron pairs of nitrogen atoms and sigma(C-N)* orbitals in these heterocage systems. Since substitution at bridge and bridgehead nitrogen atoms can be easily introduced, 1,4,6,10-tetraazaadamantane may be considered as a new rigid multivalent (3 + 1) scaffold for the design of functional molecules and materials.

引用

页码：6079 / 6086

页数：8

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