Decomposition of <I>cis</I>- and <I>trans</I>-α-Phenylcinnamoyl Peroxide and <I>t</I>-Butyl <I>cis</I>- and frans-α-Phenylperoxycinnamate. Stereochemistry of 1,2-Diphenylvinyl Radical
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概要
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Decomposition of <I>trans</I>- and <I>cis</I>-α-phenylcinnamoyl peroxide and <I>t</I>-butyl <I>trans</I>- and <I>cis</I>-α-phenylperoxycinnamate were carried out in solution and the products were determined. <I>t</I>-Butyl <I>trans</I>- and <I>cis</I>-α-phenylperoxycinnamate, on decomposition in carbon tetrachloride, gave mixtures of <I>cis</I>- and <I>trans</I>-α-chlorostilbene in the same <I>cis</I> to <I>trans</I> ratio at 110°C, but in different ratios at 80°C, the higher ratio being obtained from <I>t</I>-butyl <I>trans</I>-α-phenylperoxycinnamate. In the decomposition of <I>trans</I>- and <I>cis</I>-α-phenylcinnamoyl peroxide in various solvents at 60°C, the α-halostilbenes formed in carbon tetrachloride and bromotrichloromethane and the stilbenes produced in cumene, chloroform and triethylsilane were shown to be richer in the isomer of the same configuration as the peroxide decomposed. The stereochemical course of the reaction of the 1,2-diphenylvinyl radical generated from these peroxy-esters and peroxides is discussed.
- 公益社団法人 日本化学会の論文
著者
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Simamura Osamu
Department of Chemistry Faculty of Science The University of Tokyo
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Tokumaru Katsumi
Department of Chemistry Faculty of Science The University of Tokyo
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Wada Naoto
Department of Chemistry, Faculty of Science, The University of Tokyo
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