Transformation of Terminal Diols of Cyclic and Acyclic Saccharides to Epoxides and Alkenes by Reaction with Triphenylphosphine,Imidazole and Iodine

ABSTRACT

Reaction of various terminal diols 1,4,6,8-12, derived from cyclic and acyclic monosaccharides, with 2 mol equivalents each of TPP-imidazole-I₂ between -8 °C and 15 °C in THF afforded the corresponding epoxides 2,5,7,13-17, respectively, with 4 mol equivalents each of TPP-imidazole-I₂ in toluene at reflux temperature the starting diols afforded the corresponding alkenes 3,18-24, respectively.