4.8 Article

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

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ORGANIC LETTERS
卷 24, 期 8, 页码 1747-1751

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c00430

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  1. Ludwig-Maximilian University (LMU)
  2. Office of Naval Research (ONR) [ONR N00014-19-1-2078]
  3. Strategic Environmental Research and Development Program (SERDP) [W912HQ19C0033]

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1,1'-Diamino-5,5'-bistetrazole is a highly nitrogen-containing compound with promising energetic characteristics. It can be synthesized through a classic organic reaction protocol, which is the only Krapcho reaction on a carbamate system described in the literature. Extensive characterization and demonstration of its capability to initiate PETN have been conducted.
1,1'-Diamino-5,5'-bistetrazole (C2H4N10), 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.

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