Regioselectivity in the Diels-Alder reaction of 8,8-dimethylnaphthalene-1,4,5(8<i>H</i>)-trione with 2,4-hexadien-1-ol

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dc.contributor.authorAraya-Maturana, R
dc.contributor.authorCassels, BK
dc.contributor.authorDelgado-Castro, T
dc.contributor.authorValderrama, JA
dc.contributor.authorWeiss-López, BE
dc.date.accessioned2025-01-21T01:32:14Z
dc.date.available2025-01-21T01:32:14Z
dc.date.issued1999
dc.description.abstractThe Diels-Alder reactions of 8,8-dimethylnaphtalene-1,4,5(8H)-trione with 2,4-hexadien-1-ol and its O-acetyl derivative were investigated in different solvents. The regiochemistry of the cycloaddition of the hexadienol was determined through chemical correlation of one of the products. The solvent effect on the regioselectivity and endo/exo selectivity of this reaction is attributed to intermolecular hydrogen bonding between the hydroxyl group of the diene and the carbonyl oxygen atoms at C-4 and C-5 of the quinone in the transition state. The possible transition states have been modelled by AMI calculations in order to better interpret these experimental results. (C) 1998 Elsevier Science Ltd. All rights reserved.
dc.fuente.origenWOS
dc.identifier.issn0040-4020
dc.identifier.urihttps://repositorio.uc.cl/handle/11534/97228
dc.identifier.wosidWOS:000078026100004
dc.issue.numero3
dc.language.isoen
dc.pagina.final648
dc.pagina.inicio637
dc.revistaTetrahedron
dc.rightsacceso restringido
dc.subjectDiels-Alder reactions
dc.subjectquinones
dc.subjectregiocontrol
dc.subjecthydrogen bonding
dc.subject.ods03 Good Health and Well-being
dc.subject.odspa03 Salud y bienestar
dc.titleRegioselectivity in the Diels-Alder reaction of 8,8-dimethylnaphthalene-1,4,5(8<i>H</i>)-trione with 2,4-hexadien-1-ol
dc.typeartículo
dc.volumen55
sipa.indexWOS
sipa.trazabilidadWOS;2025-01-12
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