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

Authors
Siddiqui, MA Driscoll, JS Abushanab, E Kelley, JA Barchi, JJ Marquez, VE
Citation
Ma. Siddiqui et al., The "beta-fluorine effect" in the non-metal hydride radical deoxygenation of fluorine-containing nucleoside xanthates, NUCLEOS NUC, 19(1-2), 2000, pp. 1-12
Citations number
25
Categorie Soggetti
Biochemistry & Biophysics
Journal title
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
ISSN journal
15257770 → ACNP
Volume
19
Issue
1-2
Year of publication
2000
Pages
1 - 12
Database
ISI
SICI code
1525-7770(2000)19:1-2<1:T"EITN>2.0.ZU;2-W
Abstract
An alternative method to conduct a Barton-McCombie deoxygenation in nucleos ides Is described. The utility of the procedure is limited to structures wi th an electronegative substituent, particularly fluorine, in the beta-posit ion relative to the radical center. The process is radical in nature and tr iggered by peroxides. The abstraction of hydrogen from the solvent is favor ably influenced by the presence of a beta-fluorine.