In recent years, synthesis of azide has gained increasing attention due to the extensive biological and important industrial applications. Reactivity and selectivity of azides depends on the type functional groups attached to the nitrogen. In this project, initially, (4-(sulfonyl azide) phenyl)-1-azide with two different azide groups are synthesized. The difference in activity and selectivity are examined in a reaction with norbornene. The effect of the reaction conditions (temperature, solvent and concentration) was studied. Result of reaction between diazide 1 and one mole of norbornene gave N-(7-aza-tricyclo[3.2.1.0 2,4 ] octane)-4-(sulfonyl azide) phenyl ( 2 ) and with two moles of norbornene produced N-(4-(7-aza-tricyclo[3.2.1.0 2,4 ] octane-7-ylsulfonyl)phenyl) bicyclo [2.2.1]hept-2-en-2-amin ( 4 ). Structures of these products were elucidated with 1 H NMR, 13 C NMR and dynamic NMR. In part two, the structure of (4-(sulfonyl azide) phenyl)-1-azide, all possible intermediates, and products with norbornene was optimized using quantum chemical methods (AM1, PM3, HF and B3LYP) and 6-31G* basic set. Conformation analysis diagram was drawn (energy versus dihedral angel (F)).The energy barrier of the rotation around azide bonds with the phenyl group and several bonds in products was calculated. The NMR spectra of above compounds were calculate using GIAO method with TMS standard and compared with experimental values.