Abstract
(E)-2-[2,2-Bis(tert-butyl-NNO-azoxy)-1-(methylsulfinyl)vinyl]-1-isopropoxydiazene 1-oxide reacts with boron trifluoride etherate (BF3•Et2O) producing 2-tert-butyl-N-nitro-2H-tetrazolo-5-carboxamide 4-oxide and 2-tert-butyl-2H-tetrazolo-5-carbonitrile 4-oxide but not the expected 1,2,3,4-tetrazine 1,3-dioxide derivative. This reaction direction can be explained by cationic domino cyclization, the key stage of which is coupling of the oxodiazonium ion with the geminal MeS(O) group. Structure of N-nitrocarboxamide was confirmed by X-ray diffraction analysis.
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Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 85th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2682—2685, November, 2016.
For Part 5, see Ref. 1.
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Klenov, M.S., Churakov, A.M., Fedyanin, I.V. et al. Generation of oxodiazonium ions 6. Unexpected formation of tetrazole 1-oxides. Russ Chem Bull 65, 2682–2685 (2016). https://doi.org/10.1007/s11172-016-1636-0
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DOI: https://doi.org/10.1007/s11172-016-1636-0