Transformations of 3(4)-amino-4(3)-(tert-butyl-NNO-azoxy)furoxans in the annulation reactions into 1,2,3,4-tetrazine 1,3-dioxides
- Авторы: Zelenov V.P.1, Fedyanin I.V.2, Khakimov D.V.1, Pivina T.S.1
-
Учреждения:
- N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
- A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences
- Выпуск: Том 66, № 7 (2017)
- Страницы: 1240-1249
- Раздел: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/240944
- DOI: https://doi.org/10.1007/s11172-017-1879-4
- ID: 240944
Цитировать
Аннотация
Reactions of 3(4)-amino-4(3)-(tert-butyl-NNO-azoxy)furoxans with excess (NO2)2S2O7 or with a HNO3—H2SO4—Ac2O mixture unexpectedly produce [1,2,5]oxadiazolo[3,4-e]−[1,2,3,4]tetrazine 4,6-di-N-oxide (furazanotetrazine dioxide) and products of amino group oxidation (mainly to the corresponding azofuroxans) instead of the expected furoxanotetrazine dioxides. In some cases, individual (Z)-3,3´-((E)-diazene-1,2-diyl)-bis-((Z)-2-tert-butyl-1-oxidodiazenyl)-1,2,5-oxadiazole 2-oxide) was isolated. Formation of furazanotetrazine dioxides was observed in the reaction of 3-nitramino-4-(tert-butyl-NNO-azoxy)furoxan sodium salt with H2SO4 in Ac2O. Quantum chemical calculation at the DFT/B3LYP/6-31G(d) level of theory was used to estimate several aspects of the reactivity of 3(4)-nitramino-4(3)-(tert-butyl-NNO-azoxy)furoxans in a comparison with 3(4)-nitramino-4(3)-phenylfuroxans and the possible causes of the observed transformations were revealed.
Об авторах
V. Zelenov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Автор, ответственный за переписку.
Email: zelenov@ioc.ac.ru
Россия, 47 Leninsky prosp., Moscow, 119991
I. Fedyanin
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences
Email: zelenov@ioc.ac.ru
Россия, 28 ul. Vavilova, Moscow, 119991
D. Khakimov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: zelenov@ioc.ac.ru
Россия, 47 Leninsky prosp., Moscow, 119991
T. Pivina
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: zelenov@ioc.ac.ru
Россия, 47 Leninsky prosp., Moscow, 119991
Дополнительные файлы
