TY - JOUR
T1 - 2,3,7,8,12,13,17,18-octachloroporphyrin
AU - Senge, Mathias O.
AU - Flögel, Oliver
AU - Ruhlandt-Senge, Karin
N1 - Funding Information:
This work was supported by the Deutsche Forschungs-gemeinschaft (Se543/2-5,5-1 and Heisenberg Fellowship Se543/3-2) and the Fonds der Chemischen Industrie.
PY - 2001
Y1 - 2001
N2 - Synthesis of 3,4-dichloropyrrole and reaction with formaldehyde and p-toluene sulfonic acid catalysis, followed by oxidation with Ag2O allows a low yield entry into 2,3,7,8,12,13,17,18-octachloroporphyrin. The extremely low solubility of the free base requires work-up in the presence of metallo acetates for in situ formation of metal complexes. Utilizing this method, zinc(II) and nickel(II) complexes of the title compound were prepared as the first examples of a novel porphyrin class bearing only β-halogeno substituents. In addition, the first crystal structure of a 3,4-dihalopyrrole, 3,4-dichloropyrrole, is reported.
AB - Synthesis of 3,4-dichloropyrrole and reaction with formaldehyde and p-toluene sulfonic acid catalysis, followed by oxidation with Ag2O allows a low yield entry into 2,3,7,8,12,13,17,18-octachloroporphyrin. The extremely low solubility of the free base requires work-up in the presence of metallo acetates for in situ formation of metal complexes. Utilizing this method, zinc(II) and nickel(II) complexes of the title compound were prepared as the first examples of a novel porphyrin class bearing only β-halogeno substituents. In addition, the first crystal structure of a 3,4-dihalopyrrole, 3,4-dichloropyrrole, is reported.
KW - 2,3-dichloropyrrole
KW - Catalysis
KW - Electronic effects
KW - Halogenation
KW - β-Substituted porphyrins
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U2 - 10.1002/jpp.353
DO - 10.1002/jpp.353
M3 - Article
AN - SCOPUS:0034993589
SN - 1088-4246
VL - 5
SP - 503
EP - 506
JO - Journal of Porphyrins and Phthalocyanines
JF - Journal of Porphyrins and Phthalocyanines
IS - 6
ER -