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Conference Paper: Control of functional group proximity and direction by conformational networks: Synthesis and stereodynamics of persubstituted arenes

TitleControl of functional group proximity and direction by conformational networks: Synthesis and stereodynamics of persubstituted arenes
Authors
Keywords1,2-disubstituted-3,4,5,6- tetraethylbenzenes
1,3,5-trisubstituted-2,4,6-triethylbenzene
1,4-di-X-2,3,5,6-tetraethylbenzenes
Issue Date2001
Citation
Tetrahedron, 2001, v. 57, n. 17, p. 3615-3627 How to Cite?
AbstractThe cooperative nonbonded interactions present in hexaethylbenzene result in an arrangement of alkyl groups such that the 1,3,5 and 2,4,6 substituents point to opposite faces of the benzene ring. Correspondingly, derivatives of hexaethylbenzene have their functional groups convergent (meta as in 1,3,5-trisubstituted-2,4,6-triethylbenzene) or divergent (ortho, para as in 1,2-disubstituted-3,4,5,6-tetraethylbenzenes or 1,4-disubstituted-2,3,5,6-tetraethylbenzenes) due to this cooperative conformational network. To illustrate this structural feature and probe its dynamics, 1,4-di-X-2,3,5,6-tetraethylbenzenes have been synthesized. The dynamic stereochemistry of the disubstituted compounds has been studied by variable temperature 1H NMR spectroscopy. Using the same strategy, the 1,3,5-tris(CH2Y)-2,4,6-triethylbenzenes have also been prepared. The steric bulk of the substituent in the disubstituted compounds has been found to influence the barrier height. The trends found are applicable for the use of these compounds as angular building blocks for the design of ligands, polymers, and supramolecular architectures. © 2001 Elsevier Science Ltd.
Persistent Identifierhttp://hdl.handle.net/10722/341517
ISSN
2023 Impact Factor: 2.1
2023 SCImago Journal Rankings: 0.406
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorKilway, Kathleen V.-
dc.contributor.authorSiegel, Jay S.-
dc.date.accessioned2024-03-13T08:43:26Z-
dc.date.available2024-03-13T08:43:26Z-
dc.date.issued2001-
dc.identifier.citationTetrahedron, 2001, v. 57, n. 17, p. 3615-3627-
dc.identifier.issn0040-4020-
dc.identifier.urihttp://hdl.handle.net/10722/341517-
dc.description.abstractThe cooperative nonbonded interactions present in hexaethylbenzene result in an arrangement of alkyl groups such that the 1,3,5 and 2,4,6 substituents point to opposite faces of the benzene ring. Correspondingly, derivatives of hexaethylbenzene have their functional groups convergent (meta as in 1,3,5-trisubstituted-2,4,6-triethylbenzene) or divergent (ortho, para as in 1,2-disubstituted-3,4,5,6-tetraethylbenzenes or 1,4-disubstituted-2,3,5,6-tetraethylbenzenes) due to this cooperative conformational network. To illustrate this structural feature and probe its dynamics, 1,4-di-X-2,3,5,6-tetraethylbenzenes have been synthesized. The dynamic stereochemistry of the disubstituted compounds has been studied by variable temperature 1H NMR spectroscopy. Using the same strategy, the 1,3,5-tris(CH2Y)-2,4,6-triethylbenzenes have also been prepared. The steric bulk of the substituent in the disubstituted compounds has been found to influence the barrier height. The trends found are applicable for the use of these compounds as angular building blocks for the design of ligands, polymers, and supramolecular architectures. © 2001 Elsevier Science Ltd.-
dc.languageeng-
dc.relation.ispartofTetrahedron-
dc.subject1,2-disubstituted-3,4,5,6- tetraethylbenzenes-
dc.subject1,3,5-trisubstituted-2,4,6-triethylbenzene-
dc.subject1,4-di-X-2,3,5,6-tetraethylbenzenes-
dc.titleControl of functional group proximity and direction by conformational networks: Synthesis and stereodynamics of persubstituted arenes-
dc.typeConference_Paper-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1016/S0040-4020(01)00248-4-
dc.identifier.scopuseid_2-s2.0-0035938175-
dc.identifier.volume57-
dc.identifier.issue17-
dc.identifier.spage3615-
dc.identifier.epage3627-
dc.identifier.isiWOS:000168297500011-

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