Russian Journal of Organic Chemistry

, Volume 37, Issue 12, pp 1767–1770

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

  • A. A. Malin
  • E. V. Korchevskaya
  • M. B. Shcherbinin
  • V. A. Ostrovskii
Article

DOI: 10.1023/A:1013995011933

Cite this article as:
Malin, A.A., Korchevskaya, E.V., Shcherbinin, M.B. et al. Russian Journal of Organic Chemistry (2001) 37: 1767. doi:10.1023/A:1013995011933

Abstract

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.

Copyright information

© MAIK “Nauka/Interperiodica” 2001

Authors and Affiliations

  • A. A. Malin
    • 1
  • E. V. Korchevskaya
    • 1
  • M. B. Shcherbinin
    • 1
  • V. A. Ostrovskii
    • 1
  1. 1.St. Petersburg Technological InstituteSt. PetersburgRussia