Intermolecular reductive radical addition to 2-(2,2,2-trifluoroethylidene)-1,3-dithiane 1-oxide: experimental and theoretical studies |
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Authors: | Nakayama Ryota Matsubara Hiroshi Fujino Daishi Kobatake Takayuki Yoshida Suguru Yorimitsu Hideki Oshima Koichiro |
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Institution: | Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku Katsura, Nishikyo-ku, Kyoto 615-8510, Japan. |
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Abstract: | Tin hydride mediated radical addition of organic halide to 2-(2,2,2-trifluoroethylidene)-1,3-dithiane 1-oxide has been devised. The reaction is equivalent to an unrealizable radical addition to trifluoromethylketene, providing useful α-trifluoromethyl carbonyl equivalents. The trifluoromethyl and the sulfoxide groups of the substrate play key roles for the success of the radical addition, lowering the barrier of the radical addition step and controlling the stereoselectivity of the reaction, which DFT calculations have elucidated. |
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