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2,3,7,8,12,13,17,18-Octachloroporphyrin

Institut für Chemie, Organische Chemie, Freie Universität Berlin, Takustraße 3, D-14195 Berlin, Germany

Corresponding author, Institut für Chemie, Organische Chemie, Freie Universität Berlin, Takustraße 3, D-14195 Berlin, Germany.

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OLIVER FLÖGEL

Institut für Chemie, Organische Chemie, Freie Universität Berlin, Takustraße 3, D-14195 Berlin, Germany

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, and

KARIN RUHLANDT-SENGE

Department of Chemistry, Syracuse University, Syracuse, NY 13244, USA

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https://doi.org/10.1002/jpp.353Cited by:14 (Source: Crossref)

Abstract

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.

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