Fluoroalkyl derivatives of protected glycerol by nucleophilic substitution. Fluorine-containing amphiphilic mono- and bis-methacrylates

Article abstract of DOI:10.1016/S0022-1139(97)00063-8

The tosylate of protected glycerol (solketal, 4-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane) was fluoroalkylated by a nucleophilic substitution reaction with sodium polyfluoroalkoxides. On deprotection, 3-O-fluoroalkylated glycerol was obtained which was converted to mono- and bis-methacrylates; analogous methacrylate derivatives were prepared from 3,3,4,5,5,5-hexafluoro-pentane-1,2-diol.