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

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, H298 = 80 kJ/mol, S = -116 J× mol^{- 1} K^{- 1}, a mechanism was proposed, according to which in the rate-determining stage of S_N2 reaction triethylammonium tetrazolide attacks the C^{3 '} atom of 5'-O-benzoyl-2,3'-anhydrothymidine with simultaneous loosening of the C^{3 '}ÄO² anhydro bond.