V. Zelenov, I. Fedyanin, D. Khakimov
Nov 19, 2017
Citations
0
Influential Citations
4
Citations
Journal
Russian Chemical Bulletin
Abstract
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.