The reactions of (1-halo-1-alkenyl)dialkylboranes with lead(IV) acetate or (diacetoxyiodo)benzene. A stereoselective synthesis of 1-halo-1,2-dialkylethylenes.
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概要
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The reaction of (1-halo-1-alkenyl)dialkylboranes with lead(IV) acetate or (diacetoxyiodo)benzene was studied. (1-Bromo-1-alkenyl)dialkylboranes gave 1-bromo-1,2-dialkylethylenes. When alkyl groups on the boron atom of vinylboranes were bulky or the reaction temperatures were low, <I>Z</I>-isomers were afforded, whereas when alkyl groups on the boron atom were small or the reaction temperatures were relatively high, <I>E</I>-isomers were afforded as the main products. (1-Chloro-1-alkenyl)dialkylboranes gave (<I>Z</I>)-1-chloro-1,2-dialkylethyienes regardless of the reaction conditions. (1-Iodo-1-alkenyl)dialkylboranes failed to give satisfactory yields of 1-iodo-1,2-dialkylethylenes.
- 公益社団法人 日本化学会の論文
著者
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Masuda Yuzuru
Department Of Industrial Chemistry Kitami Institute Of Technology
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Suzuki Akira
Department Of Anesthesiology And Intensive Care Hamamatsu University School Of Medicine
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Arase Akira
Department of Applied Chemistry, Kitami Institute of Technology
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