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Article: Azaindenocorannulenes: Synthesis, Properties, and Chirality

TitleAzaindenocorannulenes: Synthesis, Properties, and Chirality
Authors
Tian, XiaoqiRoch, Loïc M.Vanthuyne, NicolasXu, JunBaldridge, Kim K.Siegel, Jay S.
Issue Date2019
Citation
Organic Letters, 2019, v. 21, n. 10, p. 3510-3513 How to Cite?
DOI: http://dx.doi.org/10.1021/acs.orglett.9b00718
AbstractPalladium-catalyzed intramolecular arylation provides bowl-shaped azaindenocorannulenes 7-9. Crystals of 8 show bowl-in-bowl columnar stacking. A substituent model rationalizes the first reduction potential of 18 related molecular bowls. The absolute configurations of bowls 7 and 9 are correlated with VCD and ECD spectra. The bowl inversion barrier of 9 (>190 kJ/mol) shows it to be more inert configurationally than chiral biaryl, phosphenes, or [n]helicenes.
Persistent Identifierhttp://hdl.handle.net/10722/341491
ISSN
1523-7060
2023 Impact Factor: 4.9
2023 SCImago Journal Rankings: 1.245
ISI Accession Number ID
WOS:000468696100009

 

DC FieldValueLanguage
dc.contributor.authorTian, Xiaoqi-
dc.contributor.authorRoch, Loïc M.-
dc.contributor.authorVanthuyne, Nicolas-
dc.contributor.authorXu, Jun-
dc.contributor.authorBaldridge, Kim K.-
dc.contributor.authorSiegel, Jay S.-
dc.date.accessioned2024-03-13T08:43:13Z-
dc.date.available2024-03-13T08:43:13Z-
dc.date.issued2019-
dc.identifier.citationOrganic Letters, 2019, v. 21, n. 10, p. 3510-3513-
dc.identifier.issn1523-7060-
dc.identifier.urihttp://hdl.handle.net/10722/341491-
dc.description.abstractPalladium-catalyzed intramolecular arylation provides bowl-shaped azaindenocorannulenes 7-9. Crystals of 8 show bowl-in-bowl columnar stacking. A substituent model rationalizes the first reduction potential of 18 related molecular bowls. The absolute configurations of bowls 7 and 9 are correlated with VCD and ECD spectra. The bowl inversion barrier of 9 (>190 kJ/mol) shows it to be more inert configurationally than chiral biaryl, phosphenes, or [n]helicenes.-
dc.languageeng-
dc.relation.ispartofOrganic Letters-
dc.titleAzaindenocorannulenes: Synthesis, Properties, and Chirality-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/acs.orglett.9b00718-
dc.identifier.pmid30995051-
dc.identifier.scopuseid_2-s2.0-85065015955-
dc.identifier.volume21-
dc.identifier.issue10-
dc.identifier.spage3510-
dc.identifier.epage3513-
dc.identifier.eissn1523-7052-
dc.identifier.isiWOS:000468696100009-

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