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Paper | Regular issue | Vol 45, No. 10, 1997, pp.1913-1919
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7915
Reaction of N-Trimethylsilylmethyliminodithiocarbonate with Carbonyl Compounds: Synthetic Equivalent of Alkylthionitrile Ylide

Makoto Oba, Masahiro Yoshihara, Jun Nagatsuka, and Kozaburo Nishiyama*

*Department of Material Science and Technology, Tokai University, 317, Nishino, Numazu, Shizuoka 410-0395, Japan


Diethyl N-trimethylsilylmethyliminodithiocarbonate (2) prepared by an addition of ethanethiol toward trimethylsilylmethyl isothiocyanate (1) followed by S-ethylation was found to react with some carbonyl compounds in the presence of fluoride ion to afford the oxazoline derivatives (4) in fair yields after a treatment of the reaction mixture with silica gel, where the dithiocarbonate derivative (2) formally served as alkylthionitrile ylide equivalent in the reaction sequence.