Reactions of Thiols with Sulfoxides. I. Scope of the Reaction and Synthetic Applications
摘要：
A detailed study on the oxidation of thiols by sulfoxides has been made. The reaction products are disulfides and sulfides (reduced sulfoxides). Of the sulfoxides investigated, dimethyl sulfoxide and tetramethylene sulfoxide were found to be the most efficient oxidizing agents. The reaction takes place with aliphatic, aralkyl, and aromatic thiols. The order of thiol reactivity was ArSH > ArCH2SH > RSH. It was also possible to oxidize dithiols by this technique. Thus 1,4-butanedithiol and 1,3-propanedithiol were oxidized to their corresponding 1,2-dithianes. Some limited mechanistic implications are presented and discussed based on the results obtained. Stoichiometrically, it has been established that 2 moles of thiol reacts with 1 mole of sulfoxide to produce 1 mole of disulfide and 1 mole of sulfide. Synthetically, it appears that aromatic thiols are selectively oxidized to their disulfides at room temperature by dimethyl sulfoxide and tetramethylene sulfoxide.
展开
DOI：
10.1021/ja01078a626
被引量：
年份：
1964
相似文献
参考文献
引证文献
辅助模式
引用
文献可以批量引用啦~
欢迎点我试用！
