5-(1,2,3-Triazol-1-yl)tetrazole derivatives of an azidotetrazole via click chemistry.
N-C bonded (non-bridged) 5-(1,2,3-triazol-1-yl)tetrazoles were synthesized by the Cu(I)-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 1 in the presence of CuSO(4)5 H(2)O and Na ascorbate at 65-70 degrees C for 48 h in CH(3)CN/H(2)O co-solvent was found to be limited to only terminal alkynes that have electron-withdrawing groups, CF(3)C[triple chemical bond]CH (2 a) and SF(5)C[triple chemical bond]CH (2 b), 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 (3 b) 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 CHCl(3), the click reaction was versatile toward alkynes even those having electron-donating groups. Properties of new products were determined and compared with those of 1. Heats of formation, detonation pressures, detonation velocities and impact sensitivities are reported for these new 5-(1,2,3-triazol-1-yl)tetrazoles.
Abe
Takashi
T
Department of Chemistry, University of Idaho, Moscow, ID 83844-2343, USA.
Tao
Guo-Hong
GH
Joo
Young-Hyuk
YH
Winter
Rolf W
RW
Gard
Gary L
GL
Shreeve
Jean'ne M
JM