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- W1996632873 abstract "An exploratory study has been made on the reaction of a number of non-branched alkenes in [D]chloroform as an aprotic solvent, using chlorosulfuric acid as reagent both in the presence and the absence of [D8]1,4-dioxane as complexing agent. Reaction of cyclopentene (1a) with 1.1 mol-equiv. of chlorosulfuric acid in [D]chloroform in the presence of 2.2 mol-equiv. of [D8]1,4-dioxane at 0 °C yielded quantitatively 1,2-cyclopentanesultone (2a). Under similar reaction conditions, the linear alkenes 1b–g afforded the corresponding β-sultones 2b–g. The ClSO3H–dioxane complex acted as a sulfonating reagent with the alkenes to yield the corresponding β-sultones in a syn cycloaddition of SO3 to the Carbon-Carbon double bond. In the absence of [D8]1,4-dioxane the reaction of the linear alkenes 1a–1k in [D]chloroform with chlorosulfuric acid at –40 °C led to the formation of the sec-alkyl chlorosulfates 5a–i, which were formed after initial protonation of the alkene by the strongly acidic ClSO3H. Cyclopentyl chlorosulfate (5a) in [D]chloroform at 0 °C was quantitatively converted into 1,2-cyclopentanesultone (2a). The sec-alkyl chlorosulfates 5b–i at 0 °C gave rise to a mixture of the internal trans- and cis-β-sultones 2b–m. Reaction of 1-octene (1g) with both acetyl sulfate (6a) and trifluoroacetyl sulfate (6b) as reagent in [D]chloroform at –20 °C directly afforded the products 1,2-octanesultone (2g), and the (E) and (Z) isomer of 2-octene-1-sulfonic acid (4g)." @default.
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- W1996632873 date "1999-01-01" @default.
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- W1996632873 title "Sulfonation of Alkenes by Chlorosulfuric Acid, Acetyl Sulfate, and Trifluoroacetyl Sulfate" @default.
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- W1996632873 doi "https://doi.org/10.1002/(sici)1099-0690(199901)1999:1<91::aid-ejoc91>3.0.co;2-j" @default.
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