Synthesis and absolute stereochemistry of (+)-6,15-dihydro-6,15-ethanonaphtho[2,3-c]pentaphene as determined by exciton chirality and X-ray Bijvoet methods.
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概要
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(6<I>R</I>,15<I>R</I>-(+)-6,15-Dihydro-6,15-ethanonaphtho[2,3-<I>c</I>]pentaphene (<B>1</B>) was synthesized from (9<I>R</I>,10<I>R</I>)-(+)-dimethyl 9,10-dihydro-9,10-ethanoanthracene-1,5-dicarboxylate, the absolute configuration of which has been established by the X-ray Bijvoet method and chemical correlations. The CD spectrum of <B>1</B> clearly exhibits very strong positive first and negative second Cotton effects due to coupling of the <SUP>1</SUP>B<SUB>b</SUB> transitions (Δε<SUB>268.0</SUB>=+931.3 and Δε<SUB>249.7</SUB>=−720.8; <I>A</I>(=Δε<SUB>1</SUB>–Δε<SUB>2</SUB>)=+1652.1), the positive sign of the <I>A</I> value being in accord with the positive exciton chirality between the two long axes of the anthracene moieties in <B>1</B>. The results demonstrate an ideal case of chiral exciton coupling in CD spectra, and provide evidence of the consistency between nonempirical CD exciton chirality and X-ray Bijvoet methods.
- 公益社団法人 日本化学会の論文
著者
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Harada Nobuyuki
Chemical Research Institute Of Nonaqueous Solutions Tohoku University:pharmaceutical Research And De
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Takuma Yuki
Chemical Laboratory Mitsubishi Chemical Industries Limited
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Uda Hisashi
Chemical Research Institute of Nonaqueous Solutions, Tohoku University
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Uda Hisashi
Chemical Research Institute Of Non-aqueous Solutions Tohoku University
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Takuma Yuki
Chemical Research Institute of Nonaqueous Solutions, Tohoku University
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Harada Nobuyuki
Chemical Research Institute of Non-aqueous Solutions, Tohoku University
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Harada Nobuyuki
Chemical Research Institute of Nonaqueous Solutions, Tohoku University
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