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Krapcho Decarboxylation of Ethyl-Carbazate: Synthetic Approach toward 1,1′-Diamino-5,5′-bistetrazole and Its Utilization as a High-Performing Metal-Free Initiator

Maximilian Benz, Thomas M. Klapötke, Jörg Stierstorfer

2022Organic Letters21 citationsDOI

Abstract

), a highly nitrogen-containing compound with promising energetic characteristics, is available through a classic organic reaction protocol applied on an inorganic azole system. This is the only Krapcho reaction on a carbamate system described in the literature so far. 1,1'-Diamino-5,5'-bistetrazole was extensively characterized through multinuclear spectroscopy, mass spectrometry, thermal analysis, and X-ray diffraction. The sensitivity values were measured, and detonation values were calculated. Its capability to initiate pentaerythritol tetranitrate (PETN) was successfully demonstrated.

Topics & Concepts

Pentaerythritol tetranitrateChemistryAzoleDetonationDecarboxylationPhysical chemistryCombinatorial chemistryOrganic chemistryExplosive materialMedicineDermatologyCatalysisAntifungalEnergetic Materials and CombustionThermal and Kinetic AnalysisChemical Reaction Mechanisms