ADVANCES IN TETRAZOLE CHEMISTRY IN RUSSIA

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

St.-Petersburg State Institute of Technology , 198013, St.Petersburg, Russia

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 = kobs ((1 + 1/It) (1 + aw KR+ (1 + 1/Ia)) ,

where It, Ia are ionization ratios of the corresponding 5-aryltetrazole and isopropyl alcohol, respectively; KR+ = -5.30 is the equilibrium constant of isopropyl cation formation from protonated isopropyl alcohol; and aw is water activity.

 

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  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).