Generation of oxodiazonium ions 4. Nitramine O-alkyl derivatives in the synthesis of benzotetrazine-1,3-dioxides

Generation of oxodiazonium ions 4. Nitramine O-alkyl derivatives in the synthesis of benzotetrazine-1,3-dioxides Full article

Journal

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

Output data

Year: 2011, Volume: 60, Number: 10, Pages: 2051-2056 Pages count : 6 DOI: 10.1007/s11172-011-0312-7

Authors

Klenov M.S. ¹ , Churakov A.M. ¹ , Strelenko Yu.A. ¹ , Tartakovsky V.A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

A new method for the synthesis of benzotetrazine-1,3-dioxides was developed from the 2-(tert-butyl-NNO-azoxy)-N-nitroaniline O-alkyl derivatives upon the action of strong acids (H2SO4, MeSO3H, CF3CO2H) or BF3·Et2O. A mechanism suggested for these reactions includes transformation of the N=N(O)OR group (R = Me, Pri) to the oxodiazonium ion (N=N=O)+, which intramolecularly reacts with the neighboring tert-butyl-NNO-azoxy group, furnishing the tetrazine-1,3-dioxide ring.

Klenov M.S. , Churakov A.M. , Strelenko Y.A. , Tartakovsky V.A.
Generation of oxodiazonium ions 4. Nitramine O-alkyl derivatives in the synthesis of benzotetrazine-1,3-dioxides
Russian Chemical Bulletin. 2011. V.60. N10. P.2051-2056. DOI: 10.1007/s11172-011-0312-7 WOS Scopus OpenAlex

≡ Web of science:	WOS:000305679700015
≡ Scopus:	2-s2.0-84864560798
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