The Stereoselectivity of the Methylcarbenoid of Zinc in the Reaction with Styrene, Indene, and Naphthalene

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概要

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• The stereoselectivity of the methylcarbenoid generated from diethylzinc and ethylidene iodide was investigated in the reactions with styrene, indene, and naphthalene. 1-Methyl-2-phenylcyclo-propanes (<I>cis</I>/<I>trans</I>=4.1) were obtained from styrene in a 13% yield. Indene gave exclusively the <I>endo</I>-isomer of 6-methyl-2,3-benzobicyclo[3.1.0]hex-2-ene in a 28% yield. From naphthalene, three isomers of 5,8-dimethyl-2,3-benzotricyclo[5.1.0.0<SUP>4,6</SUP>]oct-2-ene were obtained favorably to the <I>syn</I>-form, as in the cases with styrene and indene, but two isomers of 7-methyl-2,3-benzobicyclo[4.1.0]-hepta-2,4-diene were formed favorably to the <I>anti</I>-form. This <I>anti</I>-selectivity was explained by the step-by-step addition mechanism which had previously been proposed for the ring-expansion reaction of alkylbenzene by the methylcarbenoid.

• 公益社団法人 日本化学会の論文

著者

• Kawabata Nariyoshi

  Department of Synthetic Chemistry, Kyoto University

関連論文

• The Stereoselectivity of the Methylcarbenoid of Zinc in the Reaction with Styrene, Indene, and Naphthalene

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