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Volume 82, Issue 1
Received, 25th June, 2010, Accepted, 27th July, 2010, Published online, 29th July, 2010. |
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| Preparation of Highly Conjugated Oligoaza-PAHs Based on the Oxidative Intramolecular Coupling of Bicyclo[2.2.2]octadiene-Fused Pyrrole |
Hidemitsu Uno,* Takahiro Takiue, Hiroki Uoyama, Tetsuo Okujima, Hiroko Yamada, and Go Masuda
Department of Chemistry and Biology, Graduate School or Science and Engineering, Ehime University, Bunkyo-cho 2-5, Matsuyama 790-8577, Japan |
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Abstract
The substitution reactions of tetrafluoro-p-phthalonitrile and hexafluorobenzene with 4,7-dihydro-4,7-ethano-2H-isoindole under basic conditions afforded tetra(4,7-dihydro-4,7-ethano-2H-isoindol-2-yl)-substituted p-phthalonitrile and 1,4-difluorobenzene in good yields, respectively. Oxidative coupling reactions of these compounds gave tetra(bicycle[2.2.2]octadiene)-fused tetrapyrrolo[1,2-a;1’,2’-c;1”,2”-h;1’”,2’”-j][1,4,5,8]tetraazaanthracenes, which were then converted to tetraisoindolo[1,2-a;1’,2’-c;1”,2”-h;1’”,2’”-j]- [1,4,5,8]tetraazaanthracenes by the retro-Diels-Alder reaction. |
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Graphical Abstract
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| Corresponding author; email: uno@dpc.ehime-u.ac.jp |
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