ADVANCES IN TETRAZOLE CHEMISTRY IN RUSSIA

V.A. Ostrovskii (all other questions, proposals or information) , Michael Yudintceff (web-master)

Akylation of Tetrazoles and Tetrazolium Cations by Carbonium Ions Generated from Alcoholes

Regioselective alkylation of 5-aryltetrazoles with a -methyl- and a -arylferrocenyl alcoholes in acetic acid medium [1]

Regioselective alkylation of 5-substituted tetrazoles with isopropyl alcohole in sulfuric acid medium [2,3]

An analysis of kinetic data shows that a transition state of this reaction is protonated tetrazole.

Values of the true rate constants k were calculated by the equation:

k = k_obs ((1 + 1/I_t) (1 + a_w K_R+ (1 + 1/I_a)) ,

where I_t, I_a are ionization ratios of the corresponding 5-aryltetrazole and isopropyl alcohol, respectively; K_R+ = -5.30 is the equilibrium constant of isopropyl cation formation from protonated isopropyl alcohol; and a_w is water activity.

1. I.Yu.Shchirobokov, A.V.Sachivko,V.P.Tverdokhlebov, V.A.Ostrovskii, I.V.Tselinskii, G.I.Koldobskii, Zh.Org.Khim. 22, # 8, 1763-1768 (1986).
2. A.O.Koren, P.N.Gaponik, V.A.Ostrovskii, Int.J.Chem.Kinet., 25, # 12, 1043-1051 (1993).
3. A.O.Koren, P.N.Gaponik, V.A.Ostrovskii, Int.J.Chem.Kinet., 27, # 9, 919-924 (1995).