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Facile Ring Enlargement of Azulene to Give the Cyclopentacyclononene System by Dipolar Cycloaddition

Hafner, Klaus ; Lindner, Hans Jörg ; Ude, Werner (2023)
Facile Ring Enlargement of Azulene to Give the Cyclopentacyclononene System by Dipolar Cycloaddition.
In: Angewandte Chemie International Edition, 1979, 18 (2)
doi: 10.26083/tuprints-00022350
Article, Secondary publication, Publisher's Version

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Item Type: Article
Type of entry: Secondary publication
Title: Facile Ring Enlargement of Azulene to Give the Cyclopentacyclononene System by Dipolar Cycloaddition
Language: English
Date: 2023
Place of Publication: Darmstadt
Year of primary publication: 1979
Publisher: Wiley
Journal or Publication Title: Angewandte Chemie International Edition
Volume of the journal: 18
Issue Number: 2
DOI: 10.26083/tuprints-00022350
Corresponding Links:
Origin: Secondary publication service
Abstract:

The cyclopentacyclononene derivative (3). the first compound to contain this ring system and also the first stable cyclononatetraene not to have an annelated benzene ring, has been synthesized from the “ethanoazulene” (1). This synthesis is possible because azulene reacts readily with the ynamine (2), to give the tricyclic species (4). Although 4,6,8-methylazulene initially gives the desired ring system (5), immediate transannular bonding occurs. The bracket in (1) prevents this reaction.

Status: Publisher's Version
URN: urn:nbn:de:tuda-tuprints-223509
Classification DDC: 500 Science and mathematics > 540 Chemistry
Divisions: 07 Department of Chemistry > Clemens-Schöpf-Institut > Organ Chemistry
Date Deposited: 31 Jan 2023 10:34
Last Modified: 21 Apr 2023 11:13
URI: https://tuprints.ulb.tu-darmstadt.de/id/eprint/22350
PPN: 507135407
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