Water-soluble acylating agents: Preparation of 2-acylthio-1-alkylpyridinium salts and acylation of phenols, acids, and/or amines with these salts in an aqueous phase.

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  • Sakakibara Tohru
    Department of Chemistry, Yokohama City University
  • Watabe Yukie
    Department of Chemistry, Faculty of Science, Tokyo Institute of Technology
  • Yamada Masahide
    Department of Chemistry, Faculty of Science, Tokyo Institute of Technology
  • Sudoh Rokuro
    Department of Chemistry, Faculty of Science, Tokyo Institute of Technology

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Reaction of phenols, amines, and acids with 2-benzoylthio-1-methylpyridinium chloride prepared in situ from benzoyl chloride and 1-methyl-2(1H)-pyridinethione, afforded the corresponding benzoyl derivatives in good yields. In the reaction of p-nitrophenol, even a catalytic amount of 1-methyl-2(1H)-pyridinethione proved to be effective. Similar reactions of p-nitrophenol with isobutyryl chloride and acetyl chloride in the presence of 1-methyl-2(1H)-pyridinethione afforded p-nitrophenyl isobutyrate and p-nitrophenyl acetate in 63 and 44% yields, respectively. 2-Benzoylthio-, 2-acetylthio-, and 2-isobutyrylthio-1-ethylpyridinium tetrafluoroborates were prepared by treatment of the corresponding 2-acylthiopyridines with triethyloxonium tetrafluoroborate. These pyridinium salts also acted as acylating agents in an aqueous phase. Some competitive reactions of 2-aminoethanol and phenols with 2-benzoylthio-1-methylpyridinium chloride were also investigated.

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