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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, 1994, 127 (11)
doi: 10.26083/tuprints-00022381
Article, Secondary publication, Publisher's Version

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Chemische Berichte - November 1994 - Grieser - Synthesis and Properties of Kinetically Stabilized Cyclohepta def fluorene.pdf
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Item Type: Article
Type of entry: Secondary publication
Title: Synthesis and Properties of Kinetically Stabilized Cyclohepta[def]fluorene Derivatives
Language: English
Date: 2022
Place of Publication: Darmstadt
Year of primary publication: 1994
Publisher: Wiley
Journal or Publication Title: Chemische Berichte
Volume of the journal: 127
Issue Number: 11
DOI: 10.26083/tuprints-00022381
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Origin: Secondary publication service
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.

Uncontrolled Keywords: Cyclohepta[def]fluorene / Non-alternant pyrene isomers / Polycyclic hydrocarbon dianions
Status: Publisher's Version
URN: urn:nbn:de:tuda-tuprints-223813
Classification DDC: 500 Science and mathematics > 540 Chemistry
Divisions: 07 Department of Chemistry > Clemens-Schöpf-Institut > Organ Chemistry
Date Deposited: 28 Nov 2022 09:41
Last Modified: 21 Apr 2023 12:39
URI: https://tuprints.ulb.tu-darmstadt.de/id/eprint/22381
PPN: 507153928
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