Absolute stereochemisty and chiroptical properties of 3,3′-bis(methoxycarbonyl)-9,9′-bianthryl

被引:14
作者
Toyota, S [1 ]
Shimasaki, T [1 ]
Ueda, T [1 ]
Tanifuji, N [1 ]
Wakamatsu, K [1 ]
机构
[1] Okayama Univ Sci, Fac Sci, Dept Chem, Okayama 7000005, Japan
关键词
D O I
10.1246/bcsj.77.2065
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The axially chiral title compound was enantiomerically resolved by the diastercomer method via the camphorsultamamide of the corresponding dicarboxylic acid. The absolute stereochemistry of the (+)- and (-)-forms ([alpha](D) +32 and -33) was determined by X-ray analysis of one of the diastereomers of the sultamamide to be P and M, respectively, for the helicity about the C9-C9' bond. The observed CD and UV spectra were reasonably reproduced by the theoretical calculation based on the time-dependent density functional theory (TDDFT). The CD spectrum of the (M)-(-) form features a split curve around 270 nm assignable to the exciton coupling of the beta transition and a broad p band peak around 380 nm.
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页码:2065 / 2070
页数:6
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