Molecular transformations of unsaturated thiacrown ethers |
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Authors: | Tsuchiya Takahiro Okada Yosuke Shimizu Toshio Hirabayashi Kazunori Kamigata Nobumasa |
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Affiliation: | Department of Chemistry, Graduate School of Sciences and Engineering, Tokyo Metropolitan University, Minami-ohsawa, Hachioji, Tokyo 192-0397, Japan. |
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Abstract: | Unsaturated thiacrown ethers with 15, 18, and 21 members were oxidized to sulfoxides by the reaction with m-CPBA. The reaction with t-BuOCl at -20 degrees C also afforded sulfoxides, whereas the reaction at room temperature yielded cis-trans isomerized compounds. The cis-trans isomerized compound was also obtained by the photochemical reaction or by the reaction with NCS and NCP. Meanwhile, the reaction with NBS and NBP provided an acetal via 1,2-bridged bromonium intermediate. |
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