Premium
Reactivity of Dehydrometallophthalocyanines and ‐porphyrazines
Author(s) -
Vagin Sergei I.,
Frickenschmidt Antje,
Kammerer Bernd,
Hanack Michael
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200601056
Subject(s) - reactivity (psychology) , chemistry , medicine , pathology , alternative medicine
The zinc dehydrophthalocyanine 2 and zinc dehydrobenzoporhyrazine 8 a were generated from the 1 N ‐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 8 a 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 8 a . 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 8 a in comparison with unsubstituted benzyne towards the solvents used, such as diethyl ether and benzene.