Aromatic stacking in folded architectures through hydrogen bonding

被引:6
作者
Chen, YS [1 ]
Kampf, JW [1 ]
Lawton, RG [1 ]
机构
[1] UNIV MICHIGAN,DEPT CHEM,ANN ARBOR,MI 48109
关键词
D O I
10.1016/S0040-4039(97)01318-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The alpha, alpha'-annelation of the enamine of 1,3-hydro-2-phenalenone with methyl alpha-(bromomethyl)acrylate affords an aromatic bicyclic framework, methyl 8,9,10,11-tetrahydro-7,11-methano-12-keto-7H-cyclooocta(de)naphthalene-9-endo-carboxylate having the ester function positioned over the aromatic ring. The acid derivatives of this framework dimerize affording a ''sandwich'' structure with the H-bonded carboxyl groups between parallel naphthalene rings. The dimeric association can be easily probed using both NMR and fluorescence techniques. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:5781 / 5784
页数:4
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