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Note | Regular issue | Vol 45, No. 7, 1997, pp.1405-1410
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7824
Synthesis and Reaction of N-Trimethylsilylmethylisothiourea Derivatives as Aminonitrile Ylide Equivalents

Makoto Oba, Masahiro Yoshihara, and Kozaburo Nishiyama*

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


N-Trimethylsilylmethylisothiourea derivatives (2-5) prepared by an addition of an amine toward trimethylsilylmethyl isothiocyanate (1) followed by S-methylation were found to react with various carbonyl compounds in the presence of fluoride ion to afford the oxazoline derivatives (6-9), the formal [3+2] cycloadducts, in fair yields, in which the isothiourea derivatives served as aminonitrile ylide equivalents.