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- Publisher Website: 10.1021/ja058391a
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Article: Synthesis of fluoranthenes and indenocorannulenes: Elucidation of chiral stereoisomers on the basis of static molecular bowls
Title | Synthesis of fluoranthenes and indenocorannulenes: Elucidation of chiral stereoisomers on the basis of static molecular bowls |
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Authors | |
Issue Date | 2006 |
Citation | Journal of the American Chemical Society, 2006, v. 128, n. 21, p. 6870-6884 How to Cite? |
Abstract | Cycloaromatization of a peri diyne with an external alkyne provides a general route to indenofused polynuclear aromatics. Fluoranthenes 9 (or 13) are easily accessible in good to excellent yields (75-99%; 18 examples) from the reaction of symmetric (or asymmetric) diynes 4 and alkynes 5 (or norbornadiene) in the presence of Wilkinson's catalyst. This formal [(2+2)+2] cycloaddition can also be applied to generate various indenocorannulenes 28 from 2,3-diethynylcorannulene derivatives 27 and alkynes 5. The indenocorannulenes 28 exist in a static bowl form at room temperature with bowl-to-bowl inversion barriers higher than 24 kcal/mol. This barrier renders the rate of inversion slow enough at room temperature to establish a class of chiral, bowl-shaped stereoiomers containing no tetrahedrally ligated atoms. The crystal structure of 28g provides insight into the bowl-shaped geometry of these compounds. This new synthetic method occurs under neutral conditions and tolerates various functional groups (e.g., alkyl, aryl, alcohols, and esters). © 2006 American Chemical Society. |
Persistent Identifier | http://hdl.handle.net/10722/341087 |
ISSN | 2023 Impact Factor: 14.4 2023 SCImago Journal Rankings: 5.489 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Wu, Yao Ting | - |
dc.contributor.author | Hayama, Tomoharu | - |
dc.contributor.author | Baldridge, Kim K. | - |
dc.contributor.author | Linden, Anthony | - |
dc.contributor.author | Siegel, Jay S. | - |
dc.date.accessioned | 2024-03-13T08:40:03Z | - |
dc.date.available | 2024-03-13T08:40:03Z | - |
dc.date.issued | 2006 | - |
dc.identifier.citation | Journal of the American Chemical Society, 2006, v. 128, n. 21, p. 6870-6884 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10722/341087 | - |
dc.description.abstract | Cycloaromatization of a peri diyne with an external alkyne provides a general route to indenofused polynuclear aromatics. Fluoranthenes 9 (or 13) are easily accessible in good to excellent yields (75-99%; 18 examples) from the reaction of symmetric (or asymmetric) diynes 4 and alkynes 5 (or norbornadiene) in the presence of Wilkinson's catalyst. This formal [(2+2)+2] cycloaddition can also be applied to generate various indenocorannulenes 28 from 2,3-diethynylcorannulene derivatives 27 and alkynes 5. The indenocorannulenes 28 exist in a static bowl form at room temperature with bowl-to-bowl inversion barriers higher than 24 kcal/mol. This barrier renders the rate of inversion slow enough at room temperature to establish a class of chiral, bowl-shaped stereoiomers containing no tetrahedrally ligated atoms. The crystal structure of 28g provides insight into the bowl-shaped geometry of these compounds. This new synthetic method occurs under neutral conditions and tolerates various functional groups (e.g., alkyl, aryl, alcohols, and esters). © 2006 American Chemical Society. | - |
dc.language | eng | - |
dc.relation.ispartof | Journal of the American Chemical Society | - |
dc.title | Synthesis of fluoranthenes and indenocorannulenes: Elucidation of chiral stereoisomers on the basis of static molecular bowls | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/ja058391a | - |
dc.identifier.scopus | eid_2-s2.0-33744782312 | - |
dc.identifier.volume | 128 | - |
dc.identifier.issue | 21 | - |
dc.identifier.spage | 6870 | - |
dc.identifier.epage | 6884 | - |
dc.identifier.isi | WOS:000237816300031 | - |