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Authordc.contributor.authorAraya Maturana, Ramiro 
Authordc.contributor.authorCassels Niven, Bruce es_CL
Authordc.contributor.authorDelgado Castro, Tomás es_CL
Authordc.contributor.authorValderrama Guerrero, Jaime Adolfo es_CL
Authordc.contributor.authorWeiss López, Boris es_CL
Admission datedc.date.accessioned2009-07-02T11:25:50Z
Available datedc.date.available2009-07-02T11:25:50Z
Publication datedc.date.issued1999-01-15
Cita de ítemdc.identifier.citationTETRAHEDRON 55(3):637-648en
Identifierdc.identifier.issn0040-4020
Identifierdc.identifier.urihttp://repositorio.uchile.cl/handle/2250/120715
Abstractdc.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.en
Lenguagedc.language.isoenen
Publisherdc.publisherPERGAMON-ELSEVIER SCIENCE LTDen
Keywordsdc.subjectDiels-Alder reactionsen
Títulodc.titleRegioselectivity in the Diels-Alder reaction of 8,8-dimethylnaphthalene-1,4,5(8H)-trione with 2,4-hexadien-1-olen
Document typedc.typeArtículo de revistaen


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