Chemistry of Heterocyclic Compounds p. 1027 - 1030 (1992)
Update date:2022-08-11
Topics:
Ostrovskii, V. A.
Poplavskii, V. S.
Koldobskii, G. I.
Erusalimskii, G. B.
5-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.
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