The "β-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 β-position relative to the radical center. The process is radical in nature and trigg...

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Bibliographic Details
Published in:Nucleosides, nucleotides & nucleic acids nucleotides & nucleic acids, 2000-01, Vol.19 (1-2), p.1-12
Main Authors: Siddiqui, Maqbool A., Driscoll, John S., Abushanab, Elie, Kelley, James A., Barchi, Joseph J., Marquez, Victor E.
Format: Article
Language:English
Subjects:
AIDS/HIV
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
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Summary: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 β-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 β-fluorine.
ISSN:1525-7770
1532-2335
DOI:10.1080/15257770008032993