Reaction of 1,1-diiodoethane with copper powder in the presence of olefins and/or alkylbenzenes.

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概要

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• The treatment of 1,1-diiodoethane with copper powder in the presence of 1-heptene gave a 1.3 : 1 mixture of <I>cis</I>- and <I>trans</I>-1-methyl-2-pentylcyclopropane in 11% yield. The treatment in the presence of cyclohexene gave a 1 : 1.7 mixture of <I>endo</I>- and <I>exo</I>-7-methylbicyclo[4.1.0]heptane in 32% yield, together with 1-ethylcyclohexene in 8% yield, which was shown to be derived mainly from isomerization of the <I>endo</I>-isomer. These reactions were concluded to proceed <I>via</I> organocopper intermediate rather than free methylcarbene. The treatment of 1,1-diiodoethane with copper powder in the presence of alkylbenzene gave a mixture of <I>o</I>- and <I>p</I>-ethyl(alkyl) benzene contrary to the corresponding reaction of methylcarbenoid of zinc which gave cycloheptatriene derivatives.

• 公益社団法人 日本化学会の論文

著者

• Yamagishi Nobuyuki

  Department of Chemistry, Kyoto Institute of Technology

関連論文

• Reaction of 1,1-diiodoethane with copper powder in the presence of olefins and/or alkylbenzenes.

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