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Updated: May 16, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
A study of cyanotetrazole oxides and derivatives thereof
Franziska Boneberg1, Angie Kirchner, Thomas M Klapötke
1Department of Chemistry, Energetic Materials Research, Ludwig-Maximilian University, Butenandtstr. 5-13 (D), 81377 München, Germany.
Abstract:
In this work we report on the syntheses of energetic salts of cyanotetrazolate-1- and -2-oxides; this offers a unique ability to compare the effects of tetrazole 1- versus 2-oxidation. 5-Cyanotetrazolate-2-oxide can be synthesized by oxidation of the 5-cyanotetrazolate anion with Oxone, while the corresponding 1-oxide was synthesized by the rearrangement of azidoaminofurazan. Both chemical (multinuclear NMR, IR, and Raman spectroscopies, mass spectrometry, etc.) as well as explosive (impact, friction, and static sensitivities) properties are reported for these energetic salts. Calculated explosive performances using the EXPLO5 computer code are also reported. We furthermore detail the chemistry of these two anions, and their ability to form tetrazole-carboxamides, dihydrotetrazines, and tetrazines. The ability to hydrolyze cyanotetrazole oxides to their amides was demonstrated by two copper complexes. Several crystal structures of these species are presented in addition to full chemical characterization. Finally, the unique 1,4,-bis(2-N-oxidotetrazolate)-1,2,4,5-tetrazine anion was characterized as an energetic material as its ammonium salt.
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