5‐(1,2,3‐Triazol‐1‐yl)tetrazole Derivatives of an Azidotetrazole via Click Chemistry
- 23 September 2009
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 15 (38), 9897-9904
- https://doi.org/10.1002/chem.200901029
Abstract
NC bonded (non‐bridged) 5‐(1,2,3‐triazol‐1‐yl)tetrazoles were synthesized by the CuI‐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 CuSO4⋅5 H2O and Na ascorbate at 65–70 °C for 48 h in CH3CN/H2O co‐solvent was found to be limited to only terminal alkynes that have electron‐withdrawing groups, CF3CCH (2 a) and SF5CCH (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 °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 1. Heats of formation, detonation pressures, detonation velocities and impact sensitivities are reported for these new 5‐(1,2,3‐triazol‐1‐yl)tetrazoles.This publication has 33 references indexed in Scilit:
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