Synthesis of Tetrazino-tetrazine 1,3,6,8-Tetraoxide (TTTO)

Michael S Klenov; Alexey A Guskov; Oleg V Anikin; Aleksandr M Churakov; Yurii A Strelenko; Ivan V Fedyanin; Konstantin A Lyssenko; Vladimir A Tartakovsky

doi:10.1002/anie.201605611

Synthesis of Tetrazino-tetrazine 1,3,6,8-Tetraoxide (TTTO)

Angew Chem Int Ed Engl. 2016 Sep 12;55(38):11472-5. doi: 10.1002/anie.201605611. Epub 2016 Jul 20.

Authors

Michael S Klenov¹, Alexey A Guskov¹, Oleg V Anikin¹, Aleksandr M Churakov², Yurii A Strelenko¹, Ivan V Fedyanin³, Konstantin A Lyssenko³, Vladimir A Tartakovsky¹

Affiliations

¹ N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation.
² N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation. churakov@ioc.ac.ru.
³ A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., 119991, Moscow, Russian Federation.

PMID: 27435378
DOI: 10.1002/anie.201605611

Abstract

This study presents the first synthesis and characterization of a new high energy compound [1,2,3,4]tetrazino[5,6-e][1,2,3,4]tetrazine 1,3,6,8-tetraoxide (TTTO). It was synthesized in ten steps from 2,2-bis(tert-butyl-NNO-azoxy)acetonitrile. The synthetic strategy was based on the sequential closure of two 1,2,3,4-tetrazine 1,3-dioxide rings by the generation of oxodiazonium ions and their intramolecular coupling with tert-butyl-NNO-azoxy groups. The TTTO structure was confirmed by single-crystal X-ray.

Keywords: cyclization; energetic materials; nitrogen heterocycles; tetrazines; total synthesis.

Publication types

Research Support, Non-U.S. Gov't