Oxidative Kupplung von Hückel-Anionen: Ein einfacher Zugang zu Fulvalenen
Starting with a nearly quantitative coupling of cyclononatetraenide to 1,1’-dihydrofulvalene 3 by means of silver-tetrafluoroborate, a simple general synthetic concept for fulvalenes is outlined (Scheme 1). This plan consists in an oxidative coupling of Hueckel-anions 4 to 1,1’-dihydrofulvalenes 5...
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| Main Authors: | , , |
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| Format: | Article |
| Language: | deu |
| Published: |
Swiss Chemical Society
1983-05-01
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| Series: | CHIMIA |
| Online Access: | https://www.chimia.ch/chimia/article/view/9585 |
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| Summary: | Starting with a nearly quantitative coupling of cyclononatetraenide to 1,1’-dihydrofulvalene 3 by means of silver-tetrafluoroborate, a simple general synthetic concept for fulvalenes is outlined (Scheme 1). This plan consists in an oxidative coupling of Hueckel-anions 4 to 1,1’-dihydrofulvalenes 5 with silver(I)- or copper(II)-salts, followed by deprotonation 5 → 6 and final oxidation 6 → 7; it has been realised in the case of 1,2-3’,4’- dibenzo-pentafulvalene 1b as well as of pentafulvalene 1a. The 13C-NMR-spectra of pure 0,3-M-solutions of 1a have been recorded for the first time and are compared with those of some fulvenes. Dimerisation of the very instable 1a gives a formal [2 + 2]-cycloaddition product 12.
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| ISSN: | 0009-4293 2673-2424 |