Twin-rotor system created on a [4]radialene frame

被引：24
作者：
Kuwatani, Y
Yamamoto, G
Iyoda, M
机构：
[1] Tokyo Metropolitan Univ, Dept Chem, Grad Sch Sci, Hachioji, Tokyo 1920397, Japan
[2] Kitasato Univ, Dept Chem, Sch Sci, Sagamihara, Kanagawa 2288555, Japan
来源：
ORGANIC LETTERS | 2003年 / 5卷 / 19期
关键词：
ROTATION; CRYSTAL; DERIVATIVES; REDUCTION;
D O I：
10.1021/ol030055g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Three extended [4]radialenes with two tricyclic rings connected with exocyclic butatriene units have been synthesized. The compounds, possessing thioxanthene and dihydroanthracene moieties as the terminal substituents, show a fast rotation around the butatriene bonds at ambient temperatures (DeltaG(double dagger) = 13.7 and 14.9 kcal/mol, respectively). In contrast, the fluorene-substituted analogue shows a much higher rotational barrier (DeltaG(double dagger) = 17.8 kcal/mol) of the butatriene bonds due to the reduced steric repulsion between the two fluorene moieties at the ground state.
引用
收藏
页码：3371 / 3374
页数：4
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