Russian Journal of Organic Chemistry

, Volume 37, Issue 12, pp 1767-1770

First online:

Mechanisms of 5'-O-Benzoyl-2,3'-anhydrothymidine Reactions with Nucleophiles: II. Kinetics of the Reaction with Triethylammonium Tetrazolide in DMF

  • A. A. MalinAffiliated withSt. Petersburg Technological Institute
  • , E. V. KorchevskayaAffiliated withSt. Petersburg Technological Institute
  • , M. B. ShcherbininAffiliated withSt. Petersburg Technological Institute
  • , V. A. OstrovskiiAffiliated withSt. Petersburg Technological Institute

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The reaction of 5'-O-benzoyl-2,3'-anhydrothymidine with triethylammonium tetrazolide in DMF at 100-120°C is described by a second-order kinetic equation, following the first-order kinetics in each of the reactants. On the basis of the experimental activatin parameters, ΔH298 = 80 kJ/mol, ΔS = -116 J× mol- 1 K- 1, a mechanism was proposed, according to which in the rate-determining stage of SN2 reaction triethylammonium tetrazolide attacks the C3 ' atom of 5'-O-benzoyl-2,3'-anhydrothymidine with simultaneous loosening of the C3 'ÄO2 anhydro bond.