Tributylstannyl radical-catalyzed reaction of 1,2,3-selenadiazoles with olefins or dienes |
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Authors: | Nishiyama Yutaka Hada Yasunobu Anjiki Masahiro Miyake Kazuya Hanita Sakiko Sonoda Noboru |
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Institution: | Department of Applied Chemistry, Faculty of Engineering, Kansai University, Suita, Osaka 564-8680, Japan. nishiya@ipcku.kansai-u.ac.jp |
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Abstract: | It was found that the reaction of 1,2,3-selenadiazoles derived from cyclic ketones with olefins or dienes was markedly promoted by a catalytic amount of tributylstannyl radical, which was generated in situ from tributylstannyl hydride or allyltributylstannane and AIBN, to give the corresponding dihydroselenophenes in moderate to good yields. In contrast, when 1,2,3-selenadiazoles prepared from linear and aromatic ketones were used as substrates, the same reaction did not take place, and alkynes were formed as the sole product. |
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