4.8 Article

Synthesis and Thermal Behavior of a Fused, Tricyclic 1,2,3,4-Tetrazine Ring System

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 44, Pages 12973-12975

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201506744

Keywords

1,2,3,4-tetrazines; 1,2,4-triazoles; amination; oxidation; energetic materials

Funding

  1. Joint Munitions Technolgy Development Program
  2. U.S. Department of Energy [DE-AC52-06A25396]
  3. Office of Naval Research [N00014-11-AF-0-0002]

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This study presents the synthesis and characterization of a fused, tricyclic 1,2,3,4-tetrazine ring system. The molecule is synthesized in a three-step process from 5,5-dinitro-bis,1,2,4-triazole via a di-N-amino compound. Oxidation to form the azo-coupled fused tricyclic 1,2,3,4-tetrazine is achieved using tert-butyl hypochlorite as the oxidant. The di-N-amino compound and the desired fused tricyclic 1,2,3,4-triazine display interesting thermal behavior and are predicted to be high-performance energetic materials.

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