1,3,2-Dioxathiolane 2,2-Dioxide

Abstract

(R1 = R2 = H) [1072-53-3] C2H4O4S (MW 124.13) (R1 = R2 = n-Bu) [127901-92-3] C10H20O4S (MW 236.37) (display epoxide-like reactivity;2, 3 nucleophilic displacement of both oxygen functions is feasible4-6) Alternate Names: ethylene sulfate; cyclic sulfates. Preparative Method: cyclic sulfates of 1,2-diols (1,3,2-dioxathiolane 2,2-dioxides) are most easily prepared in a two-step procedure (eq 1).2 Reaction of a 1,2-diol with Thionyl Chloride leads to a cyclic sulfite which is then oxidized to the corresponding cyclic sulfate 1. Direct conversion of a 1,2-diol to a cyclic sulfate using Sulfuryl Chloride is generally less efficient.2, 3 (1) Handling, Storage, and Precautions: the structural similarity between cyclic sulfates and Dimethyl Sulfate must be recognized. Dimethyl sulfate, and to a lesser extent ethylene sulfate, are carcinogenic and potent alkylating agents that are toxic by inhalation and ingestion.1 Cyclic sulfates must, as a result, be treated with extreme care.