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Communication | Regular issue | Vol 55, No. 2, 2001, pp.249-254
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9131
Cycloaddition of New N-Unsubstituted Azomethine Ylides Generated from N-[(Trimethylsilyl)methyl]thiocarbamates, Synthetic Equivalents of Non-stabilized Alkoxy- or Alkylthionitrile Ylides

Otohiko Tsuge,* Taizo Hatta, Masanori Shinozuka, and Hideki Tashiro

*Department of Applied Chemistry, Sojo University, 4-22-1, Ikeda, Kumamoto-shi, 860-0082, Japan

Abstract

The reaction of (trimethylsilyl)methyl isothiocyanate with alcohol in the presence of aluminum alkoxide provides a useful route for the preparation of N-[(trimethylsilyl)methyl]thiocarbamates. The S-methylation of thiocarbamates followed by desilylation generates nonstabilized azomethine ylides having both methylthio and alkoxy groups at the ylide carbon. These azomethine ylides react with electron-deficient carbon-carbon multiples bonds to give formal alkoxynitrile ylide- and/or methylthionitrile ylide-cycloadducts. Thus, the azomethine ylides can be synthetic equivalents of nonstabilized alkoxy- or methylthionitrile ylides that are otherwise relatively inaccessible.