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Communication | Regular issue | Vol 38, No. 6, 1994, pp.1217-1220
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6705
Fluoride Ion Promoted Azomethine Ylid Generation from 1-Methyl-2-[methylthio(trimethylsilylmethylimino)methylimino]-1,2-dihydropyridine, a Synthetic Equivalent of Aminonitrile Ylid

Shinya Kohra* and Yoshinori Tominaga

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


1-Methyl-2-[methylthio(trimethylsilylmethylimino)methylimino]-1,2-dihydropyridine (1), prepared from 2-amino-1-methylpyridinium iodide in 3 steps, reacted with carbonyl compounds in the presence of cesium fluoride in acetonitrile to give 2-(1-methyl-1,2-dihydropyridylidene)aminooxazoline derivatives (6) via the 1,3-dipolar cycloaddition. This reaction was the first example of reaction of aminonitrile ylid with the C=O double bond.