Mechanisms of 5'-O-Benzoyl-2,3'-anhydrothymidine Reactions with Nucleophiles: II. Kinetics of the Reaction with Triethylammonium Tetrazolide in DMF
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- Malin, A.A., Korchevskaya, E.V., Shcherbinin, M.B. et al. Russian Journal of Organic Chemistry (2001) 37: 1767. doi:10.1023/A:1013995011933
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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, ΔH≠298 = 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.