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Communication | Regular issue | Vol 23, No. 10, 1985, pp.2489-2492
Published online, 1st January, 1970
DOI: 10.3987/R-1985-10-2489
Water-induced Azomethiene Ylide Generation from N-(Silylmethyl)thioimidates, Synthetic Equivalents of Nonstabilized Nitrile Ylides

Otohiko Tsuge,* Shuji Kanemasa, Toshiaki Yamada, and Koyo Matsuda

*Research Institute of Industrial Science, Faculty of Engineering, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan


N-(Silylmethyl)thioimidates undergo a water-induced desilylation generating azomethine ylide 1,3-dipoles which cycloadd to a variety of electron-deficient olefins providing 1- or 2-pyrrolines after the elimination of thiol, indicating that the thioimidates are synthetic equivalents of nonstabilized nitrile ylides.