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Communication | Regular issue | Vol 36, No. 7, 1993, pp.1497-1500
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6383
Reaction of 2-Trimethylsilylmethylthiopyridine Promoted by a Fluoride Ion: The First Example of Generation of 2-Pyridylthiomethylcarbanion

Shinya Kohra,* Hiroshi Ueda, and Yoshinori Tominaga

*Faculty of Liberal Arts, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan


2-Trimethylsilylmethylthiopyridine prepared readily by the reaction of 2-mercaptopyridine with chloromethyltrimethylsilane in the presence of potassium carbonate reacts with carbonyl compounds in the presence of a catalytic amount of tetrabutylammonium fluoride (TBAF) to give 2-(2-pyridylthio)ethanols. This reaction is the first example of generation and introduction of 2-pyridylthiomethylcarbanion.