SYNTHESIS OF PHTHALOCYANINE FUSED WITH BICYCLO[2.2.2]OCTADIENES AND THERMAL CONVERSION INTO NAPHTHALOCYANINE

摘要

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 naphthalocyamne 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.