Synthesis and absolute stereochemistry of (+)-7,14-dihydro-7,14-ethanodibenz[a,h]anthracene and its derivatives.
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概要
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(7<I>R</I>,14<I>R</I>)-(+)-7,14-Dihydro-7,14-ethanodibenz[<I>a</I>,<I>h</I>]anthracene (<B>1</B>), and the 2,9-dimethyl- (<B>2</B>) and 2,4,9,11-tetramethyl- (<B>3</B>) derivatives were synthesized from (9<I>R</I>,10<I>R</I>)-(+)-9,10-dihydro-9,10-ethanoanthracene-1,5-dicarbaldehyde (<B>4</B>) of known absolute configuration. The CD spectra of <B>1</B>, <B>2</B>, and <B>3</B> clearly exhibit positive first and negative second Cotton effects due to the coupling of the <SUP>1</SUP>B<SUB>b</SUB> transitions of two naphthalene chromophores: Δε<SUB>237.0</SUB>=+326.5, Δε<SUB>224.0</SUB>=−180.5, <I>A</I>=+507.0, for <B>1</B>; Δε<SUB>240.6</SUB>=+371.5, Δε<SUB>227.0</SUB>=−149.4, <I>A</I>=+520.9, for <B>2</B>; Δε<SUB>242.0</SUB>=+340.3, Δε<SUB>225.0</SUB>=−88.0, <I>A</I>=+428.3, for <B>3</B>. Since the sign of the A values is positive, positive exciton chirality between the two long axes of the naphthalene moieties is assigned. The (7<I>R</I>,14<I>R</I>) absolute configuration of <B>1</B>, <B>2</B>, and <B>3</B> is established by both 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 Non-aqueous Solutions Tohoku University
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