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The Thiophene Analogue of Porphyrin: Tetrathiaporphyrin Dication

✍ Scribed by Prof. Dr. Emanuel Vogel; Peter Röhrig; Martin Sicken; Bernd Knipp; Adalbert Herrmann; Michael Pohl; Dr. Hans Schmickler; Dr. Johann Lex

Book ID
102726628
Publisher
John Wiley and Sons
Year
1989
Tongue
English
Weight
619 KB
Volume
28
Category
Article
ISSN
0044-8249

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✦ Synopsis

In spite of the long history of porphyrin chemistry,"] tetraoxaporphyrin 1, unlike porphyrin a dicationic species, was discovered only last year.[21 The synthesis of 1 (as perchlorate 1 a)-in the variant to be presented here-is surprising in its simplicity, for the compound can readily be prepared starting from furfuryl alcohol in merely a two-step sequence modeled after the biogenesis of porphyrin. 1 qualifies spectroscopically and in structural respects as an aromatic porphyrin, while its chemical behavior, as to be expected for a molecule with a carbenium ion/oxonium ion structure, is characterized by high reactivity towards nucleophiles.

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The preparation and properties of thioph
The preparation and properties of thiophen analogues of porphyrins and related systems. Part II synthesis of porphyrinogen analogues
✍ M. Ahmed; O. Meth-Cohn 📂 Article 📅 1969 🏛 Elsevier Science 🌐 French ⚖ 202 KB

Although the ahemistry and synthesis of the porphyrin ring system has been intensively investigated for more than fifty years, no reports have yet appeared regarding its thiophen isosteres. We report below the first syntheses of the thiophen isosteres of the porphyrinogen system (I).