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

Authors:Francisco, Cosme G.
González Martín, Concepción C.
Rodríguez Paz, Nieves
Suárez, Ernesto
Issue Date:4-Oct-2003
Publisher:American Chemical Society
Citation:Organic Letters 5(22): 4171-4173 (2003)
Abstract:The 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.
Description:3 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
Appears in Collections:(IPNA) Artículos

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