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Paper | Special issue | Vol 82, No. 1, 2010, pp.791-802
Published online, 29th July, 2010
DOI: 10.3987/COM-10-S(E)69
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

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.