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Die Protonierung von 1-Formyl- und 1-Acetyl-azulenen

Meuche, Doris ; Dreyer, D. ; Hafner, Klaus ; Heilbronner, E. (2023)
Die Protonierung von 1-Formyl- und 1-Acetyl-azulenen.
In: Helvetica chimica acta, 1967, 50 (4)
doi: 10.26083/tuprints-00022405
Article, Secondary publication, Publisher's Version

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Item Type: Article
Type of entry: Secondary publication
Title: Die Protonierung von 1-Formyl- und 1-Acetyl-azulenen
Language: German
Date: 21 March 2023
Place of Publication: Darmstadt
Year of primary publication: 1967
Publisher: Wiley-VCH
Journal or Publication Title: Helvetica chimica acta
Volume of the journal: 50
Issue Number: 4
DOI: 10.26083/tuprints-00022405
Corresponding Links:
Origin: Secondary publication service

NMR. data show that protonation of 1-formyl-azulene yields essentially a one-to-one mixture of conjugate acids in which the hydroxyl group assumes the syn-planar or anti-planar configuration relative to the tropylium nucleus. The presence of a minute amount of protonation in position 3 is demonstrated by the rapid hydrogendeuterium exchange in this position. Steric interference in 1-formyl-azulenes with a methyl group in the peri position 8 favours the anti-planar configuration. As shown by one example, the conjugate acids of 1-acetyl-azulenes without substituents in positions 2 or 8 assume the anti-planar configuration. In 1-acetyl-azulenes carrying a methyl group in position 8, addition of a proton to the carbon centre 1 is the preferred route of protonation, as a consequence of the accompanying strain release

Status: Publisher's Version
URN: urn:nbn:de:tuda-tuprints-224051
Classification DDC: 500 Science and mathematics > 540 Chemistry
Divisions: 07 Department of Chemistry > Clemens-Schöpf-Institut > Organ Chemistry
Date Deposited: 21 Mar 2023 10:21
Last Modified: 18 Oct 2023 11:05
URI: https://tuprints.ulb.tu-darmstadt.de/id/eprint/22405
PPN: 512322872
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