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Communication | Regular issue | Vol 19, No. 12, 1982, pp.2259-2262
Published online, 1st January, 1970
DOI: 10.3987/R-1982-12-2259
Cycloaddition Reactions of Thiazolium N-Dicyanomethylide with Olefinic Dipolarophiles

Otohiko Tsuge, Yoichi Shimizu, Hiroshi Shimoharada, and Shuji Kanemasa

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


The cycloaddition reaction of a stable N-methylide, thiazolium N-dicyanomethylide, with acyclic olefinic dipolarophiles such as dimethyl fumarate, maleate, and trans-1,2-dibenzoylethylene proceeded in a stereoselective manner to give only the corresponding endo-[3 + 2] cycloadducts, all of which were stable in boiling tetrahydrofurn. In the reaction of the methylide with N-substituted maleimides, however, a mixture of endo- and exo-[3 + 2] cycloadducts, whose relative yields changed with the reaction time, was formed. The endo cycloadduct was found to isomerize into the exo cycloadduct in tetrahydrofuran even at room temperature.