The "beta-fluorine effect" in the non-metal hydride radical deoxygenation of fluorine-containing nucleoside xanthates

Nucleosides Nucleotides Nucleic Acids. 2000 Jan-Feb;19(1-2):1-12. doi: 10.1080/15257770008032993.

Abstract

An alternative method to conduct a Barton-McCombie deoxygenation in nucleosides is described. The utility of the procedure is limited to structures with an electronegative substituent, particularly fluorine, in the beta-position relative to the radical center. The process is radical in nature and triggered by peroxides. The abstraction of hydrogen from the solvent is favorably influenced by the presence of a beta-fluorine.

MeSH terms

  • Anti-HIV Agents / chemical synthesis*
  • Dideoxyadenosine / analogs & derivatives*
  • Dideoxyadenosine / chemical synthesis
  • Fluorine / chemistry*
  • Free Radicals / chemistry
  • Hydrogen
  • Magnetic Resonance Spectroscopy
  • Oxidation-Reduction
  • Stereoisomerism
  • Structure-Activity Relationship
  • Thiones / chemical synthesis*

Substances

  • Anti-HIV Agents
  • Free Radicals
  • Thiones
  • Fluorine
  • lodenosine
  • Dideoxyadenosine
  • Hydrogen