Generation of oxodiazonium ions 6. Unexpected formation of tetrazole 1-oxides

Generation of oxodiazonium ions 6. Unexpected formation of tetrazole 1-oxides Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2016, Volume: 65, Number: 11, Pages: 2682-2685 Pages count : 4 DOI: 10.1007/s11172-016-1636-0

Authors

Klenov M.S. ¹ , Churakov A.M. ¹ , Fedyanin I.V. ² , Tartakovsky V.A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991 Moscow, Russian Federation

(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.

Klenov M.S. , Churakov A.M. , Fedyanin I.V. , Tartakovsky V.A.
Generation of oxodiazonium ions 6. Unexpected formation of tetrazole 1-oxides
Russian Chemical Bulletin. 2016. V.65. N11. P.2682-2685. DOI: 10.1007/s11172-016-1636-0 WOS Scopus OpenAlex

≡ Web of science:	WOS:000401572700019
≡ Scopus:	2-s2.0-85019255918
≡ OpenAlex:	W2616564727