Alkenes from Cyclic Sulfates and Thionocarbonates of 1,2-Diols via Tellurium Chemistry

Article abstract of DOI:10.1016/0040-4039(95)01532-M

Treatment of 1,2-diol cyclic sulfates (1,3,2-dioxathiolane 2,2-dioxides) with telluride ion, generated in situ by reduction of the element, yields alkenes rapidly (10 min - 2 h) under mild conditions (0 deg C to room temperature).The reaction is stereospecific, e. g. meso-2,3-diphenylethane-2,3-diol -> cis-stilbene; d,l-2,3-diphenylethane-2,3-diol -> trans-stilbene.Unsaturated mannose and ribose derivatives have been obtained, and diethyl (-)-tartrate gives diethyl fumarate.The reaction may be performed with 0,1 equiv or less of elemental tellurium in the presence of a stoichiometric amount of reducing agent.Reaction of telluride ion with cyclic thionocarbonates (1,3-dioxolane-2-thiones) of meso- and d,l-1,2-diphenylethane-1,2-diol yields cis- and trans-stilbene, respectively.