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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. (Publisher's Version)
In: Chemische Berichte, 127 (11), pp. 2307-2314. Wiley, e-ISSN 1099-0682,
DOI: 10.26083/tuprints-00022381,
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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
Origin: Secondary publication service
Status: Publisher's Version
Title: Synthesis and Properties of Kinetically Stabilized Cyclohepta[def]fluorene Derivatives
Language: English
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.

Journal or Publication Title: Chemische Berichte
Volume of the journal: 127
Issue Number: 11
Place of Publication: Darmstadt
Publisher: Wiley
Uncontrolled Keywords: Cyclohepta[def]fluorene / Non-alternant pyrene isomers / Polycyclic hydrocarbon dianions
Classification DDC: 500 Naturwissenschaften und Mathematik > 540 Chemie
Divisions: 07 Department of Chemistry > Organ Chemistry
Date Deposited: 28 Nov 2022 09:41
Last Modified: 28 Nov 2022 09:42
DOI: 10.26083/tuprints-00022381
Corresponding Links:
URN: urn:nbn:de:tuda-tuprints-223813
URI: https://tuprints.ulb.tu-darmstadt.de/id/eprint/22381
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