One-Step Synthesis of Esters of Aliphatic β-Chloro Sulfonic Acids. Their Sequential Conversion to Other Sulfonic Acid Derivatives

Article abstract of DOI:10.1021/je00031a036

A one-step synthesis of methyl 2-chlorohexane-1- and 2-chlorooctane-1-sulfonate by the novel free-radical addition of methyl chlorosulfonate to 1-hexene and 1-octene, respectively, is reported.These products were converted by standard techniques into the corresponding sodium and benzylthiuronium β-chlorosulfonic acid salts and sulfonyl chlorides.Dehydrochlorination of these latter products with triethylamine affored regiospecific formation of trans-α,β-unsaturated sulfonyl chlorides, which were transformed by conventional methods into sodium and benzylthiuroniumunsaturated and saturated sulfonic acid salts.Eleven new compositions of matter are reported.