Department of Chemistry, University of Idaho, Moscow, ID 83844-2343, USA.
Chemistry. 2009 Sep 28;15(38):9897-904. doi: 10.1002/chem.200901029.
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.
N-C 键合（非桥接）5-(1,2,3-三唑-1-基)四唑是通过 Cu(I)催化的 1,3-偶极氮丙啶-炔点击反应，使用 5-叠氮-N-(异丙叉基)-1H-四唑（1）合成的。例如，在 65-70°C 下，1 在 CuSO4·5H2O 和 Na 抗坏血酸盐存在下，在 CH3CN/H2O 共溶剂中反应 48 小时，发现该反应仅限于具有吸电子基团的末端炔烃，CF3C[三重键]CH（2a）和 SF5C[三重键]CH（2b），生成异丙叉基-[5-(4-三氟甲基-1,2,3-三唑-1-基)四唑-1-基]胺（3a）和异丙叉基-[5-(4-五氟硫基-1,2,3-三唑-1-基)四唑-1-基]胺（3b），产率分别为 47%和 66%。当在 0°C 下使用 CuI 和 2,6-联吡啶作为催化剂，在 CHCl3 中反应 13 小时时，点击反应对炔烃具有通用性，甚至对具有供电子基团的炔烃也具有通用性。测定了新产物的性质，并与 1 进行了比较。报道了这些新的 5-(1,2,3-三唑-1-基)四唑的生成热、爆轰压力、爆轰速度和撞击感度。
