Synthesis, resolution and determination of energy barriers to rotation of atropisomeric, planar-chiral [n]paracyclophanes by dynamic enantioselective gas chromatography and computer simulation

被引:37
作者
Hochmuth, DH [1 ]
König, WA [1 ]
机构
[1] Univ Hamburg, Inst Organ Chem, D-20146 Hamburg, Germany
关键词
D O I
10.1016/S0957-4166(99)00092-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
We herein report on the synthesis of substituted carbocyclic [11]paracyclophanes, which are planar-chiral and atropisomeric. Their energy barrier to rotation was determined by dynamic enantioselective gas chromatography on selectively modified cyclodextrins as chiral stationary phases and subsequent computer simulation of the plateau-shaped elution profiles (DGC-CS). The energy barriers are compared with those of analogous dioxa[11]paracyclophanes. (C) 1999 Elsevier Science Ltd. All rights reserved.
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页码:1089 / 1097
页数:9
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