The "beta-fluorine effect" in the non-metal hydride radical deoxygenation of fluorine-containing nucleoside xanthates.
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.
Siddiqui
M A
MA
Laboratory of Medicinal Chemistry, National Cancer Institute, NIH, Bethesda, MD 20892, USA.
Driscoll
J S
JS
Abushanab
E
E
Kelley
J A
JA
Barchi
J J
JJ
Marquez
V E
VE
D019380:Anti-HIV Agents / Q000138:chemical synthesis*; D016048:Dideoxyadenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D005461:Fluorine / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D006859:Hydrogen; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013871:Thiones / Q000138:chemical synthesis*
D019380:Anti-HIV Agents; D005609:Free Radicals; D013871:Thiones; D005461:Fluorine; C073072:lodenosine; D016048:Dideoxyadenosine; D006859:Hydrogen