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

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

Журнал

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Вых. Данные

Год: 2014, Том: 79, Номер: 13, Страницы: 6079-6086 Страниц : 8 DOI: 10.1021/jo5007703

Авторы

Semakin Artem N. ¹ , Sukhorukov Alexey Yu. ¹ , Nelyubina Yulia V. ² , Khomutova Yulia A. ¹ , Ioffe Sema L. ¹ , Tartakovsky Vladimir A. ¹

Организации

1	N.D. Zelinsky Institute of Organic Chemistry , Leninsky prospect 47, 119991, Moscow, Russia.
2	A.N. Nesmeyanov Institute of Organoelement Compounds, Vavilov str. 28, 119991, Moscow, Russia.

The first synthesis of 1,4,6,10-tetraazaadamantane, the C3v-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 σ*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.

Semakin A.N. , Sukhorukov A.Y. , Nelyubina Y.V. , Khomutova Y.A. , Ioffe S.L. , Tartakovsky V.A.
Urotropine Isomer (1,4,6,10-Tetraazaadamantane): Synthesis, Structure, and Chemistry
Journal of Organic Chemistry. 2014. V.79. N13. P.6079-6086. DOI: 10.1021/jo5007703 WOS Scopus OpenAlex

Web of science:	WOS:000338693300016
Scopus:	2-s2.0-84903721281
OpenAlex:	W2326525650

БД	Цитирований
OpenAlex	20
Scopus	17
Web of science	16