Grieser, Udo ; Hafner, Klaus (2022)
Synthesis and Properties of Kinetically Stabilized Cyclohepta[def]fluorene Derivatives.
In: Chemische Berichte, 1994, 127 (11)
doi: 10.26083/tuprints-00022381
Artikel, Zweitveröffentlichung, Verlagsversion
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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: | 2022 |
Autor(en): | Grieser, Udo ; Hafner, Klaus |
Art des Eintrags: | Zweitveröffentlichung |
Titel: | Synthesis and Properties of Kinetically Stabilized Cyclohepta[def]fluorene Derivatives |
Sprache: | Englisch |
Publikationsjahr: | 2022 |
Ort: | Darmstadt |
Publikationsdatum der Erstveröffentlichung: | 1994 |
Verlag: | Wiley |
Titel der Zeitschrift, Zeitung oder Schriftenreihe: | Chemische Berichte |
Jahrgang/Volume einer Zeitschrift: | 127 |
(Heft-)Nummer: | 11 |
DOI: | 10.26083/tuprints-00022381 |
URL / URN: | https://tuprints.ulb.tu-darmstadt.de/22381 |
Zugehörige Links: | |
Herkunft: | Zweitveröffentlichungsservice |
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 |
Status: | Verlagsversion |
URN: | urn:nbn:de:tuda-tuprints-223813 |
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: | 28 Nov 2022 09:41 |
Letzte Änderung: | 02 Aug 2024 12:45 |
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