Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 38, Pages 9897-9904Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200901029
Keywords
azoles; click chemistry; energetic materials; heterocyclic compounds; tetrazoles
Categories
Funding
- DTRA [HDTRA1-07-1-0024]
- NSF [CHE-0315275]
- ONR [N00014-06-1-1032]
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N-C bonded (non-bridged) 5-(1,2,3-triazol-1-yl)tetrazoles were synthesized by the Cu-1-catalyzed 1,3-dipolar azide-alkyne cycloaddition click reaction using 5-azido-N-(propan-2-ylidene)-1H-tetrazole (1). For example, the click reaction of I in the presence of CuSO4 center dot 5H(2)O and Na ascorbate at 65-70 degrees C for 48 h in CH3CN/H2O co-solvent was found to be limited to only terminal alkynes that have electron-withdrawing groups, CF3C CH (2a) and SF5C CH (2b), giving rise to isopropylidene-[5-(4-trifluoromethyl-1,2,3-triazol-1-yl)tetrazol-1-yl]amine (3 a) and isopropylidene-[5-(4-pentafluorosulfanyl-1,2,3-triazol-1-yl)tetrazol-1-yl]-amine (3b) in 47% and 66% yields, respectively. When carried out under conditions using CuI and 2,6-lutidine as catalysts at 0 degrees C for 13 h in CHCl3, the click reaction was versatile toward alkynes even those having electron-donating groups. Properties of new products were determined and compared with those of L Heats of formation, detonation pressures, detonation velocities and impact sensitivities are reported for these new 5-(1,2,3-triazol-1-yl)tetrazoles.
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