Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 13, Issue 3, Pages 985-991Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200601056
Keywords
benzyne; dehydrobenzoporphyrazines; dehydrophthalocyanines; phthalocyanines; zinc
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The zinc dehydrophthalocyanine 2 and zinc dehydrobenzoporhyrazinc 8a were generated from the 1N-aminobenzotriazole-annulated zinc phtalocyanine 1 and zinc benzoporhyrazine 8, respectively, by oxidation with Pb(OAc)(4), in different solvents, for example, diethyl ether, tetrahydrofuran, acetic acid, and benzene. The reactivity of 2 and 8a was studied in detail. These species not only easily undergo Diels-Alder additions with dienes, but also the used solvents can be added. Among the addition products with solvents ethoxy-, acetoxy-, acetoxybutyloxy-substituted and barrelen-fused phthalocyanines and benzoporpyrazines were isolated. No products resulting from the dimerization of two dehydro species were observed either for 2 or 8a. Analysis of the reaction products in comparison with those obtained by oxidation of 1-aminobenzotriazole 15 under similar conditions proves a higher reactivity (electrophilicity) of the dehydro-PcZn 2 and dehydro-PzZn 8a in comparison with unsubstituted benzyne towards the solvents used, such as diethyl ether and benzene.
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