Oxygen-accelerated generation of the bromocarbenoid reagent of zinc from diethylzinc and bromoform. Bromocyclopropanes from olefins.

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概要

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• Oxygen greatly accelerates the generation of the bromocarbenoid reagent of zinc from diethylzinc and bromoform. Olefins, including cyclohexene, cyclooctene, 1-hexene, <I>cis</I>- and <I>trans</I>-2-butene, isobutene, and 2-methyl-2-butene were bromocyclopropanated in yields of <I>ca.</I> 60–85% using a diethylzinc-bromoform-oxygen system. The bromocarbenoid showed high <I>syn</I>-selectivity for the addition to cyclooctene and <I>cis</I>-2-butene. 9-Bromo-9-deutero[6.1.0]nonane was obtained from cyclooctene using CDBr<SUB>3</SUB>. Styrene inhibited the formation of the bromocarbenoid reagent and polymerized under the reaction conditions, suggesting a free radical chain mechanism for the formation of the carbenoid reagent.

• 公益社団法人 日本化学会の論文

著者

• Hashimoto Harukichi

  Department of Applied Chemistry, Faculty of Engineering, Tohoko University

• Miyano Sotaro

  Department of Applied Chemistry, Faculty of Engineering, Tohoku University

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