Thermal ring-opening reaction of N-polynitromethyl tetrazoles: facile generation of nitrilimines and their reactivity

Thermal ring-opening reaction of N-polynitromethyl tetrazoles: facile generation of nitrilimines and their reactivity Full article

Journal

Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416

Output data

Year: 2009, Volume: 65, Number: 17, Pages: 3441-3445 Pages count : 5 DOI: 10.1016/j.tet.2009.02.032

Authors

Semenov V.V. ¹ , Kanischev M.I. ¹ , Shevelev S.A. ¹ , Kiselyov A.S. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, RAS, Moscow 119991, Leninsky Pr. 47, Russia

Thermal ring-opening reaction of N-(R-dinitromethyl)-5-nitrotetrazoles (R=NO2, F, Cl) yielded highly reactive N-(R-dinitromethyl)-nitrilimine intermediates under mild conditions. These species underwent facile and regiospecific reaction with nitriles and acetylenes to afford the corresponding nitrotriazoles and nitropyrazoles in 50–90% yields. Treatment of N-(chlorodinitromethyl)-5-nitrotetrazole with the excess of azide led to a unique compound with the molecular formula C2N14. Based on the analytical data, it was assigned a structure of diazidomethylenecarbonohydrazonic diazide.

Semenov V.V. , Kanischev M.I. , Shevelev S.A. , Kiselyov A.S.
Thermal ring-opening reaction of N-polynitromethyl tetrazoles: facile generation of nitrilimines and their reactivity
Tetrahedron. 2009. V.65. N17. P.3441-3445. DOI: 10.1016/j.tet.2009.02.032 WOS Scopus OpenAlex

Web of science:	WOS:000265175100013
Scopus:	2-s2.0-62749178998
OpenAlex:	W1979025404

DB	Citing
OpenAlex	32
Scopus	40
Web of science	29