Iptycene quinones: Synthesis and structure

被引:81
作者
Zhu, XZ
Chen, CF [1 ]
机构
[1] Chinese Acad Sci, Inst Chem, Ctr Mol Sci, Beijing 100080, Peoples R China
[2] Chinese Acad Sci, Grad Sch, Beijing 100080, Peoples R China
关键词
D O I
10.1021/jo0483015
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical and efficient method to synthesize iptycene quinones has been developed. As a result, a series of pentiptycene quinones 8-16 were conveniently synthesized by one-pot reaction of triptycene quinone 4 or 5 with anthracene 1 or its derivatives 2-3 in refluxing acetic acid in the presence of p-chloranil, followed by CAN oxidative demethylation. Similarly, a series of heptiptycene quinones 17-23 with U-shaped cavities were achieved with pentiptycene quinone 10 and triptycene diquinone 6 as precursors. Non-iptycene triquinones 24 with one tweezer-shaped cavity and 25 with two U-shaped cavities were synthesized by one-pot reactions of anthracene with pentiptycene triquinones 16a and 16b, respectively. Non-iptycene triquinone 26 with a dendritic structure was conveniently obtained by the reaction of anthracene with either pentiptycene diquinone 12 or triptycene triquinone 7. The structures of regioisomers 16a and 16b were determined by the single-crystal structure analysis of 16b. The structures of other regioisomers, including heptiptycene tetraquinones 19a/19b/19c and heptiptycene triquinones 23a/23b, were identified by comparative reactions.
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页码:917 / 924
页数:8
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