Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

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


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.