Reactivity features of ortho-Carboranillithium towards 3,6-Diaryl-1,2,4,5-Tetrazines

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Abstract

The reaction of ortho-carboranillithium with 3,6-di(2-pyridyl)-1,2,4,5-tetrazine, considered as an example of the “from challenging to simple” strategy in the chemistry of carbonanes, leads to the previously unknown 3-ortho-carboranyl-[1,2,3]triazolo[1,5-a]pyridine as a result of cleavage of the tetrazine cycle and subsequent formation of the triazole cycle with nitrogen elimination. The structure of the obtained compound was confirmed by the spectroscopic and X-ray diffraction studies. The reaction mechanism, which was additionally confirmed by quantum-chemical calculations of electron densities and the Fukui function, was proposed.

About the authors

T. D. Moseev

Institute of Chemical Engineering, Ural Federal University; I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; South Ural State University

Email: timofey.moseev@urfu.ru
Yekaterinburg, Russia; Yekaterinburg, Russia; Chelyabinsk, Russia

D. S. Kopchuk

Institute of Chemical Engineering, Ural Federal University; I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; South Ural State University

Yekaterinburg, Russia; Yekaterinburg, Russia; Chelyabinsk, Russia

L. A. Smyshliaeva

Institute of Chemical Engineering, Ural Federal University; I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; South Ural State University

Yekaterinburg, Russia; Yekaterinburg, Russia; Chelyabinsk, Russia

A. N. Tsmokaluk

Institute of Chemical Engineering, Ural Federal University; I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; South Ural State University

Yekaterinburg, Russia; Yekaterinburg, Russia; Chelyabinsk, Russia

P. A. Slepukhin

Institute of Chemical Engineering, Ural Federal University; I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; South Ural State University

Yekaterinburg, Russia; Yekaterinburg, Russia; Chelyabinsk, Russia

A. V. Rybakova

Institute of Chemical Engineering, Ural Federal University; I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; South Ural State University

Yekaterinburg, Russia; Yekaterinburg, Russia; Chelyabinsk, Russia

G. V. Zyryanov

Institute of Chemical Engineering, Ural Federal University; I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; South Ural State University

Yekaterinburg, Russia; Yekaterinburg, Russia; Chelyabinsk, Russia

M. V. Varaksin

Institute of Chemical Engineering, Ural Federal University; I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; South Ural State University

Yekaterinburg, Russia; Yekaterinburg, Russia; Chelyabinsk, Russia

V. N. Charushin

Institute of Chemical Engineering, Ural Federal University; I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; South Ural State University

Yekaterinburg, Russia; Yekaterinburg, Russia; Chelyabinsk, Russia

O. N. Chupakhin

Institute of Chemical Engineering, Ural Federal University; I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; South Ural State University

Yekaterinburg, Russia; Yekaterinburg, Russia; Chelyabinsk, Russia

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