Tetraoxaporphycene Dication
The well known, extremely reactive [18]annulene 1 and the hypothetical isomer 2 should be capable of being stabilized by CH2‐ and CHCH‐groups as internal and external bridges, respectively. The corresponding hydrocarbons, 3 and 4, are still unknown, although they are of great interest as links betw...
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Veröffentlicht in: | Angewandte Chemie International Edition 1988-03, Vol.27 (3), p.411-414 |
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Hauptverfasser: | , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | The well known, extremely reactive [18]annulene 1 and the hypothetical isomer 2 should be capable of being stabilized by CH2‐ and CHCH‐groups as internal and external bridges, respectively. The corresponding hydrocarbons, 3 and 4, are still unknown, although they are of great interest as links between the non‐natural annulenes and the porphyrin 5 or the porphycene 6 recently synthesized for the first time. It has now been possible to prepare the tetraoxa analogues of 5 and 6, i.e. the dications 7 and 8. In both cases they could be isolated as the perchlorates and structurally characterized, revealing their relationship with 5 and 6, respectively. In the synthesis of 7 the decisive step was a MacDonald condensation, followed directly by an oxidation, whereas the route to 8 led via a McMurry coupling and subsequent oxidation. Reaction of 2,2′‐difurylmethane with formaldehyde afforded tetraoxaporphyrinogen in low yield, which could be oxidized with nitric acid to the tetraoxaporphyrin. |
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ISSN: | 0570-0833 1521-3773 |
DOI: | 10.1002/anie.198804111 |