Grieser, Udo ; Hafner, Klaus (1994)
Synthesis and Properties of Kinetically Stabilized Cyclohepta[def]fluorene Derivatives.
In: Chemische Berichte, 127 (11)
doi: 10.1002/cber.1491271132
Artikel, Bibliographie
Dies ist die neueste Version dieses Eintrags.
Kurzbeschreibung (Abstract)
The dihydrocyclohepta[def]fluorene 18 was prepared by starting from 2,7-di-tert-butylfluorene (11). Deprotonation of 18 furnished the dianion 3²⁻ in which the charge is mainly localized at the five- and seven-membered rings as evidenced by NMR investigations. Attempts to oxidize 3²⁻ to the uncharged species 3 failed. The ketones 26 and 29 were obtained by regioselective oxidation of 18. Deprotonation of 29 and 26 furnished the anions 4 and 5, respectively, which could be described as cyclohepta[def]fluorenes with a strong donor substituent. ¹³C-NMR spectroscopic investigations, however, revealed that 4 is described best as an acyl-substituted fluorenyl anion. In contrast to this, proof of the existence of the anion 5 could be obtained only from a trapping experiment.
| Typ des Eintrags: | Artikel |
|---|---|
| Erschienen: | 1994 |
| Autor(en): | Grieser, Udo ; Hafner, Klaus |
| Art des Eintrags: | Bibliographie |
| Titel: | Synthesis and Properties of Kinetically Stabilized Cyclohepta[def]fluorene Derivatives |
| Sprache: | Englisch |
| Publikationsjahr: | 1994 |
| Ort: | Darmstadt |
| Verlag: | Wiley |
| Titel der Zeitschrift, Zeitung oder Schriftenreihe: | Chemische Berichte |
| Jahrgang/Volume einer Zeitschrift: | 127 |
| (Heft-)Nummer: | 11 |
| DOI: | 10.1002/cber.1491271132 |
| Zugehörige Links: | |
| Kurzbeschreibung (Abstract): | The dihydrocyclohepta[def]fluorene 18 was prepared by starting from 2,7-di-tert-butylfluorene (11). Deprotonation of 18 furnished the dianion 3²⁻ in which the charge is mainly localized at the five- and seven-membered rings as evidenced by NMR investigations. Attempts to oxidize 3²⁻ to the uncharged species 3 failed. The ketones 26 and 29 were obtained by regioselective oxidation of 18. Deprotonation of 29 and 26 furnished the anions 4 and 5, respectively, which could be described as cyclohepta[def]fluorenes with a strong donor substituent. ¹³C-NMR spectroscopic investigations, however, revealed that 4 is described best as an acyl-substituted fluorenyl anion. In contrast to this, proof of the existence of the anion 5 could be obtained only from a trapping experiment. |
| Freie Schlagworte: | Cyclohepta[def]fluorene / Non-alternant pyrene isomers / Polycyclic hydrocarbon dianions |
| Sachgruppe der Dewey Dezimalklassifikatin (DDC): | 500 Naturwissenschaften und Mathematik > 540 Chemie |
| Fachbereich(e)/-gebiet(e): | 07 Fachbereich Chemie 07 Fachbereich Chemie > Clemens-Schöpf-Institut 07 Fachbereich Chemie > Clemens-Schöpf-Institut > Fachgebiet Organische Chemie |
| Hinterlegungsdatum: | 02 Aug 2024 12:45 |
| Letzte Änderung: | 02 Aug 2024 12:45 |
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Verfügbare Versionen dieses Eintrags
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Synthesis and Properties of Kinetically Stabilized Cyclohepta[def]fluorene Derivatives. (deposited 28 Nov 2022 09:41)
- Synthesis and Properties of Kinetically Stabilized Cyclohepta[def]fluorene Derivatives. (deposited 02 Aug 2024 12:45) [Gegenwärtig angezeigt]
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