1,3-Dipolar cycloadditions of C₈₂ (C_2v) with N-methylazomethine have been studied at the PM3 level, and their mechanism and regiochemistry were investigated. Calculational analyses of these reactions show that 1,3-dipolar cycloadditions of C₈₂ with N-methylazomethine follow a stepwise mechanism and these reactions are exothermic. The activation barrier of the reactions is increased as the bond length of the reaction site is enlarged. Not only from energetics but also from thermodynamic point of view, the most favored reaction site is the bond with the shortest length and the largest strain.

Key words: C₈₂, cycloaddition, mechanism