Tetrazoles. 31. Kinetics of the reaction of nitriles with alkylammonium azides. Formation of 5-substituted tetrazoles
Abstract5-Substituted tetrazoles are formed by the reaction of nitriles with mono-, di-, and trialkylammonium azides in aprotic dipolar solvents and alcohols. Tetraalkylammonium azides do not react with nitriles. The formation of 5-substituted tetrazoles occurs by a 1,3-dipolar cycloaddition mechanism. Electron-accepting substituents increase the reactivity of nitriles significantly while the structure of the alkylammonium azide and the solvent polarity have no significant effect on the reaction rate.