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The Thiophene Analogue of Porphyrin: Tetrathiaporphyrin Dication
Author(s) -
Vogel Emanuel,
Röhrig Peter,
Sicken Martin,
Knipp Bernd,
Herrmann Adalbert,
Pohl Michael,
Schmickler Hans,
Lex Johann
Publication year - 1989
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198916511
Subject(s) - dication , chemistry , furfuryl alcohol , porphyrin , sulfur , ring (chemistry) , photochemistry , thiophene , planarity testing , organic chemistry , crystallography , ion , catalysis
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.