Syntheses of 9‐vinylated benzotropolones by a sequence of acylation, ring‐closing enyne metathesis, and oxidation
Abstract: Previous studies from our group revealed that 6,7-benzannulated nona-1,8-diene-5-ones of a variety of substitution patterns undergo ring-closing diene metatheses in the presence of the Grubbs-II catalyst; the benzocycloheptadienones formed thereby gave benzotropolones in between one and four follow-up steps. The present study discloses that exemplary 6,7-benzannulated non-1-en-8-yn-5-ones undergo ring-closing enyne metatheses in the presence of the Grubbs-II catalyst; the vinylated benzocycloheptadienones formed thereby gave 9-vinylbenzotropolones in four steps: silyl enol ether formation, Rubottom-type oxidation, desilylation, and Dess-Martin oxidation. The metathesis substrates were synthesized either from (ortho-bromoaryl)ethynes with an unsubstituted sp-carbon by a Br→Li exchange and an acylation with an H2C=CH-containing Weinreb amide; or, they were synthesized from (ortho-bromoaryl)ethynes with a trimethylsilylated sp-carbon by a Br→Li→ZnHal exchange, an acylation with an H2C=CH-containing thioester, and a desilylation
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Anmerkungen
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ChemistrySelect. - 8, 33 (2023) , e202301748, ISSN: 2365-6549
- Ereignis
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Veröffentlichung
- (wo)
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Freiburg
- (wer)
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Universität
- (wann)
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2023
- Urheber
- DOI
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10.1002/slct.202301748
- URN
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urn:nbn:de:bsz:25-freidok-2396739
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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25.03.2025, 13:54 MEZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Momm, Sarah N.
- Seifried, Christian
- Brückner, Reinhard
- Universität
Entstanden
- 2023
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