The Thiophene Analogue of Porphyrin: Tetrathiaporphyrin Dication

Furfuryl alcohol can be transformed in a simple way into the long‐awaited sulfur analog of porphyrin, the tetrathiaporphyrin dication 1, isolated as the perchlorate. The key to the synthesis is a remarkably straightforward sulfur/oxygen exchange in tetraoxaporphyrinogen. As would be expected from th...

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Veröffentlicht in:Angewandte Chemie International Edition 1989-12, Vol.28 (12), p.1651-1655
Hauptverfasser: Vogel, Emanuel, Röhrig, Peter, Sicken, Martin, Knipp, Bernd, Herrmann, Adalbert, Pohl, Michael, Schmickler, Hans, Lex, Johann
Format: Artikel
Sprache:eng
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Zusammenfassung:Furfuryl alcohol can be transformed in a simple way into the long‐awaited sulfur analog of porphyrin, the tetrathiaporphyrin dication 1, isolated as the perchlorate. The key to the synthesis is a remarkably straightforward sulfur/oxygen exchange in tetraoxaporphyrinogen. As would be expected from the relatively large van der Waals radius of sulfur, the transformation from the tetraoxaporphyrin dication to 1 is accompanied by loss of planarity in the ring system.
ISSN:0570-0833
1521-3773
DOI:10.1002/anie.198916511