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Paper | Special issue | Vol 74, No. 1, 2007, pp.835-842
Published online, 30th October, 2007
DOI: 10.3987/COM-07-S(W)75
Synthesis of Phthalocyanine Fused with Bicyclo[2.2.2]octadienes and Thermal Conversion into Naphthalocyanine

Taiji Akiyama, Atsuko Hirao, Tetsuo Okujima, Hiroko Yamada, Hidemitsu Uno, and Noboru Ono*

*Department of Chemistry, Faculty of Science, Ehime University, Matsuyama 790-8577, Japan

Abstract

Mg complex of phthalocyanine fused with bicyclo[2.2.2]octadiene (BCOD) units is prepared by the reaction of BCOD-fused phthalonitrile with Mg(OPr)2 in PrOH at 100 °C overnight in 42% yield. Subsequent heating the product at 250 °C results in clean formation naphthalocyanine via the retro Diels-Alder reaction. An attempt to the synthesis of BCOD-fused tetraazaporphyrin by the similar cyclization of the Diels-Alder adduct of dicyanoacetylene with 1,3-cyclohexadiene was unsuccessful.