T. Sakakibara, Yukie Watabe, Masahide Yamada
1988
Citations
0
Influential Citations
4
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
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.