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

Abstract

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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