Reaction of dimethyl sulfoxide-trifluoroacetic anhydride with anilines, phenols, and thiophenols.

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  • Hiraki Yuji
    Department of Chemistry, Faculty of Science, Kyoto University
  • Kamiya Masahiro
    Department of Chemistry, Faculty of Science, Kyoto University
  • Tanikaga Rikuhei
    Department of Chemistry, Faculty of Science, Kyoto University
  • Ono Noboru
    Department of Chemistry, Faculty of Science, Kyoto University
  • Kaji Aritsune
    Department of Chemistry, Faculty of Science, Kyoto University

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  • ChemInform Abstract: REACTION OF DIMETHYL SULFOXIDE‐TRIFLUOROACETIC ANHYDRIDE WITH ANILINES, PHENOLS, AND THIOPHENOLS

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The reaction of dimethyl sulfoxide–trifluoroacetic anhydride complex with anilines, phenols, and thiophenols was studied, and the following results were obtained. (1) The yields of a methylthiomethylated product were improved with anilines. The reaction proceeded without significant amount of tar, the unreacted anilines being easily recovered. (2) Selective ortho-methylthiomethylation took place with phenols in good yields at lower temperature, para-methylthiomethylation occurring at higher temperature. (3) Methylthiomethylation took place with thiophenols on a sulfur atom of thiophenol at room temperature in a simple process.

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