Fragmentation of carbohydrate anomeric alkoxyl radicals: a new synthesis of 1,1-difluoro-1-iodo alditols.
[reaction: see text]. The beta-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.
Instituto de Productos Naturales y Agrobiología del C.S.I.C., Carretera de La Esperanza 3, 38206 La Laguna, Tenerife, Spain.
Cosme G
CG
Francisco
Concepción C
CC
González
Nieves R
NR
Paz
Ernesto
E
Suárez
D000438:Alcohols / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis*; D007455:Iodine / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry*; D013402:Sugar Alcohols / Q000138:chemical synthesis*
D000438:Alcohols; D006846:Hydrocarbons, Halogenated; D009005:Monosaccharides; D013402:Sugar Alcohols; C059688:alkoxyl radical; D005461:Fluorine; D007455:Iodine