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Toward the Synthesis of Tetrazino‐­tetrazine 1,3,6,8‐Tetraoxide (TTTO): An Approach to Non‐annulated 1,2,3,4‐Tetrazine 1,3‐Dioxides Full article

Journal European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690
Output data Year: 2015, Volume: 2015, Number: 28, Pages: 6170-6179 Pages count : 10 DOI: 10.1002/ejoc.201500923
Authors Klenov Michael S. 1 , Anikin Oleg V. 1 , Churakov Aleksandr M. 1 , Strelenko Yurii A. 1 , Fedyanin Ivan V. 2 , Ananyev Ivan V. 2 , Tartakovsky Vladimir A. 1
Affiliations
1 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation http://zioc.ru/?lang=en
2 A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., 119991 Moscow, Russian Federation

Abstract: A novel approach for the synthesis of 6-(tert-butyl-NNO-azoxy)-5-methylthio-1,2,3,4-tetrazine 1,3-dioxide (1) was developed. This compound is likely to be a precursor of tetrazino-tetrazine 1,3,6,8-tetraoxide. The synthetic strategy consists of four steps: a synthesis of bis(tert-butyl-NNO-azoxy)methane, coupling of the latter with dimethyl nitrodithioimidocarbonate to give N-nitroimine 3, O-alkylation of the latter to O-alkylated nitroenamine and its reaction with BF3·Et2O to afford tetrazine 1,3-dioxide 1. An X-ray diffraction study of 1 was accomplished.
Cite: Klenov M.S. , Anikin O.V. , Churakov A.M. , Strelenko Y.A. , Fedyanin I.V. , Ananyev I.V. , Tartakovsky V.A.
Toward the Synthesis of Tetrazino‐­tetrazine 1,3,6,8‐Tetraoxide (TTTO): An Approach to Non‐annulated 1,2,3,4‐Tetrazine 1,3‐Dioxides
European Journal of Organic Chemistry. 2015. V.2015. N28. P.6170-6179. DOI: 10.1002/ejoc.201500923 WOS Scopus OpenAlex
Identifiers:
≡ Web of science: WOS:000362747900008
≡ Scopus: 2-s2.0-84942500605
≡ OpenAlex: W1701250731
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