Acetalation studies. Part IXΦ. Reaction of sucrose and some related sugars with acetone in the presence of iodine; a novel cleavage-isopropylidenation methodψ†‡

An efficient cleavage-isopropylidenation reaction of sucrose, catalyzed by iodine, is described. Related D-fructofuranosyl-containing oligosaccharides, some common disaccharides and their individual monosaccharide units were treated in a similar manner to yield isopropylidenated monosaccharide derivatives. The reaction conditions are particularly mild and selective. Some mechanistic aspects of the procedure are also discussed.