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| Title: | Fragmentation of carbohydrate anomeric alkoxyl radicals: a new synthesis of 1,1-difluoro-1-iodo alditols |
Authors: | Francisco, Cosme G. CSIC; González Martín, Concepción C. CSIC ORCID ; Rodríguez Paz, Nieves CSIC ; Suárez, Ernesto CSIC ORCID | 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 | URI: | http://hdl.handle.net/10261/16764 | DOI: | 10.1021/ol035611l | ISSN: | 1523-7060 |
| Appears in Collections: | (IPNA) Artículos |
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