<p>Ethyl 12-chlorosulfodehydroabietate was used in the first synthesis of hydroxysulfonamides containing monoethanolamine and phenylalaninol fragments in 98% and 95% yields, respectively. <i>p</i>-Toluenesulfonyl derivatives of these hydroxysulfonamides were found to react with potassium thioacetate to be converted to thioacetates. However, they underwent quantitative conversion to disulfides in the presence of trace amounts of pyridine. Both thioacetates and disulfides were oxidized with chlorine dioxide to sulfonyl chlorides in 90–96% yields.</p>

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Pyridine-mediated synthesis of dehydroabietane-derived disulfides and their oxidation with chlorine dioxide to sulfonyl chlorides

  • E. S. Izmest’ev,
  • S. V. Pestova,
  • D. V. Petukhov,
  • S. A. Rubtsova

摘要

Ethyl 12-chlorosulfodehydroabietate was used in the first synthesis of hydroxysulfonamides containing monoethanolamine and phenylalaninol fragments in 98% and 95% yields, respectively. p-Toluenesulfonyl derivatives of these hydroxysulfonamides were found to react with potassium thioacetate to be converted to thioacetates. However, they underwent quantitative conversion to disulfides in the presence of trace amounts of pyridine. Both thioacetates and disulfides were oxidized with chlorine dioxide to sulfonyl chlorides in 90–96% yields.