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Energetic Functionalized Azido/Nitro Imidazole Fused 1,2,3,4‐Tetrazine
Author(s) -
Tang Yongxing,
He Chunlin,
Yin Ping,
Imler Gregory H.,
Parrish Damon A.,
Shreeve Jean'ne M.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800347
Subject(s) - tetrazine , chemistry , imidazole , nitro , tricyclic , ring (chemistry) , crystal structure , stereochemistry , energetic material , combinatorial chemistry , crystallography , medicinal chemistry , explosive material , organic chemistry , alkyl
Despite the high potential of the azo‐coupled fused tricyclic 1,2,3,4‐tetrazine ring system in energetic materials, there are only very limited examples of such a scaffold. The oxidation of di‐ N ‐amino compound 1 with tert ‐butyl hypochlorite ( t BuOCl) gives rise to the unexpected chloro‐substituted compound 2 , which behaves as a precursor to the structurally attractive diazido/nitro‐substituted fused tricyclic 1,2,3,4‐tetrazine 3 . The structure is well characterized and is supported by single‐crystal X‐ray diffraction. Compound 3 was found to be a highly energetic and sensitive explosive.