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Synthesis and Properties of Kinetically Stabilized Cyclohepta[def]fluorene Derivatives

Grieser, Udo ; Hafner, Klaus (2022)
Synthesis and Properties of Kinetically Stabilized Cyclohepta[def]fluorene Derivatives.
In: Chemische Berichte, 127 (11)
doi: 10.26083/tuprints-00022381
Artikel, Zweitveröffentlichung, Verlagsversion

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
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
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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 > Fachgebiet Organische Chemie
Hinterlegungsdatum: 28 Nov 2022 09:41
Letzte Änderung: 29 Nov 2022 06:22
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