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Ionic Liquids as Unique Solvents in One‐Pot Synthesis of 4‐( N ,2,2,2‐Tetranitroethylamino)‐3‐R‐Furazans
Author(s) -
Sheremetev Aleksei B.,
Aleksandrova Nataly S.,
Palysaeva Nadezhda V.,
Struchkova Marina I.,
Tartakovsky Vladimir A.,
Suponitsky Kyrill Yu.
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201302126
Subject(s) - nitration , chemistry , detonation , ionic liquid , mannich base , oxygen balance , mannich reaction , ionic bonding , condensation , crystal structure , crystallography , medicinal chemistry , oxygen , ion , organic chemistry , catalysis , explosive material , physics , thermodynamics
An efficient two‐step one‐pot protocol for the synthesis of N‐nitrated trinitroethylamino furazans in an ionic liquid has been developed involving the condensation of aminofurazans with trinitroethanol and the N‐nitration of an intermediate Mannich base. Trinitroethylnitramino derivatives have been synthesized and characterized by multinuclear NMR spectroscopy and X‐ray crystallography. A role of the N ,2,2,2‐tetranitroethylamino group for stabilization of the high‐density crystal‐packing motif is described. The performance calculations gave detonation pressures and velocities for the furazan derivatives in a range of about 31–36 GPa and 8330–8745 ms −1 , respectively, which makes them competitive energetic materials. Furthermore, due to the positive oxygen balance, the compounds could be potential oxidizers for energetic formulations.