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• W2153407879 abstract "(R1 = R2 = H) [1072-53-3] C2H4O4S (MW 124.13) InChI = 1S/C2H4O4S/c3-7(4)5-1-2-6-7/h1-2H2 InChIKey = ZPFAVCIQZKRBGF-UHFFFAOYSA-N (R1 = R2 = n-Bu) [127901-92-3] C10H20O4S (MW 236.37) InChI = 1S/C10H20O4S/c1-3-5-7-9-10(8-6-4-2)14-15(11,12)13-9/h9-10H,3-8H2,1-2H3/t9-,10-/m1/s1 InChIKey = UNBCRBGPJKMSKH-NXEZZACHSA-N (display epoxide-like reactivity;2, 3 nucleophilic displacement of both oxygen functions is feasible4-6) Alternate Names: ethylene glycol cyclic sulfate; ethylene sulfate; 1,2-ethylene sulfate; cyclic sulfates. Preparative Methods: 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 However, with the cyclic sulfates bearing functionalities that are easily subjected to RuO4-catalyzed oxidation, the direct conversion of diols to cyclic sulfates with Sulfuryl Chloride is favored.14 (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." @default.
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• W2153407879 date "2009-03-15" @default.
• W2153407879 modified "2023-09-27" @default.
• W2153407879 title "1,3,2-Dioxathiolane 2,2-Dioxide" @default.
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• W2153407879 doi "https://doi.org/10.1002/047084289x.rd405s.pub2" @default.
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