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Title

Fragmentation of carbohydrate anomeric alkoxyl radicals: a new synthesis of 1,1-difluoro-1-iodo alditols

AuthorsFrancisco, Cosme G. ; González Martín, Concepción C. ; Rodríguez Paz, Nieves ; Suárez, Ernesto
Issue Date4-Oct-2003
PublisherAmerican Chemical Society
CitationOrganic Letters 5(22): 4171-4173 (2003)
AbstractThe β-fragmentation of 2,2-difluoro-saccharide anomeric alkoxyl radicals, generated under oxidative condition by treatment of the respective alcohols with (diacetoxyiodo)benzene (DIB) and iodine, afforded 1,1-difluoro-1-iodo alditols in high yield. The reactivity of the fluorinated radical generated by rupture of the C−I bond has been preliminarily assessed by reductive deiodination with tributyltin hydride/AIBN and intermolecular allylation using the Keck reaction.
Description3 pages, 1 table, 2 schemes.-- PMID: 14572277 [PubMed].-- Printed version published Oct 30, 2003.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/ol035611l
Publisher version (URL)http://dx.doi.org/10.1021/ol035611l
URIhttp://hdl.handle.net/10261/16764
DOI10.1021/ol035611l
ISSN1523-7060
Appears in Collections:(IPNA) Artículos
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