Regioselectivity in the acylation of methylhydroquinone dimethyl ether: An unprecedented case of indirect steric hindrance

Detalhes bibliográficos
Autor(a) principal: MacEdo, Fernando C.
Data de Publicação: 2011
Outros Autores: Andrei, César Cornélio, Campiom, Danilo, Ishikawa, Noemia Kazue
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional do INPA
Texto Completo: https://repositorio.inpa.gov.br/handle/1/16205
Resumo: The origin of the highly regioselective acylation of methylhydroquinone dimethyl ether was investigated using geometry minimization (ab initio and DFT) and NOE spectroscopic measurements. The theoretical and experimental results were consistent with the indirect participation of the aromatic methyl group in blocking the electrophile attack at position 3 of the aromatic ring. © 2011 Elsevier Ltd. All rights reserved.
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spelling MacEdo, Fernando C.Andrei, César CornélioCampiom, DaniloIshikawa, Noemia Kazue2020-05-31T18:05:42Z2020-05-31T18:05:42Z2011https://repositorio.inpa.gov.br/handle/1/1620510.1016/j.tetlet.2011.01.130The origin of the highly regioselective acylation of methylhydroquinone dimethyl ether was investigated using geometry minimization (ab initio and DFT) and NOE spectroscopic measurements. The theoretical and experimental results were consistent with the indirect participation of the aromatic methyl group in blocking the electrophile attack at position 3 of the aromatic ring. © 2011 Elsevier Ltd. All rights reserved.Volume 52, Número 14, Pags. 1612-1614Attribution-NonCommercial-NoDerivs 3.0 Brazilhttp://creativecommons.org/licenses/by-nc-nd/3.0/br/info:eu-repo/semantics/openAccessAromatic CompoundDimethyl EtherElectrophileHydroquinone DerivativeMethyl GroupAb Initio CalculationAcylationDensity Functional TheoryNuclear Overhauser EffectRing OpeningStereochemistryStereospecificityRegioselectivity in the acylation of methylhydroquinone dimethyl ether: An unprecedented case of indirect steric hindranceinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleTetrahedron Lettersengreponame:Repositório Institucional do INPAinstname:Instituto Nacional de Pesquisas da Amazônia (INPA)instacron:INPAORIGINALartigo-inpa.pdfartigo-inpa.pdfapplication/pdf291353https://repositorio.inpa.gov.br/bitstream/1/16205/1/artigo-inpa.pdfa75cdb593f5ae24bdd4953db285299a9MD511/162052020-05-31 14:10:49.297oai:repositorio:1/16205Repositório de PublicaçõesPUBhttps://repositorio.inpa.gov.br/oai/requestopendoar:2020-05-31T18:10:49Repositório Institucional do INPA - Instituto Nacional de Pesquisas da Amazônia (INPA)false
dc.title.en.fl_str_mv Regioselectivity in the acylation of methylhydroquinone dimethyl ether: An unprecedented case of indirect steric hindrance
title Regioselectivity in the acylation of methylhydroquinone dimethyl ether: An unprecedented case of indirect steric hindrance
spellingShingle Regioselectivity in the acylation of methylhydroquinone dimethyl ether: An unprecedented case of indirect steric hindrance
MacEdo, Fernando C.
Aromatic Compound
Dimethyl Ether
Electrophile
Hydroquinone Derivative
Methyl Group
Ab Initio Calculation
Acylation
Density Functional Theory
Nuclear Overhauser Effect
Ring Opening
Stereochemistry
Stereospecificity
title_short Regioselectivity in the acylation of methylhydroquinone dimethyl ether: An unprecedented case of indirect steric hindrance
title_full Regioselectivity in the acylation of methylhydroquinone dimethyl ether: An unprecedented case of indirect steric hindrance
title_fullStr Regioselectivity in the acylation of methylhydroquinone dimethyl ether: An unprecedented case of indirect steric hindrance
title_full_unstemmed Regioselectivity in the acylation of methylhydroquinone dimethyl ether: An unprecedented case of indirect steric hindrance
title_sort Regioselectivity in the acylation of methylhydroquinone dimethyl ether: An unprecedented case of indirect steric hindrance
author MacEdo, Fernando C.
author_facet MacEdo, Fernando C.
Andrei, César Cornélio
Campiom, Danilo
Ishikawa, Noemia Kazue
author_role author
author2 Andrei, César Cornélio
Campiom, Danilo
Ishikawa, Noemia Kazue
author2_role author
author
author
dc.contributor.author.fl_str_mv MacEdo, Fernando C.
Andrei, César Cornélio
Campiom, Danilo
Ishikawa, Noemia Kazue
dc.subject.eng.fl_str_mv Aromatic Compound
Dimethyl Ether
Electrophile
Hydroquinone Derivative
Methyl Group
Ab Initio Calculation
Acylation
Density Functional Theory
Nuclear Overhauser Effect
Ring Opening
Stereochemistry
Stereospecificity
topic Aromatic Compound
Dimethyl Ether
Electrophile
Hydroquinone Derivative
Methyl Group
Ab Initio Calculation
Acylation
Density Functional Theory
Nuclear Overhauser Effect
Ring Opening
Stereochemistry
Stereospecificity
description The origin of the highly regioselective acylation of methylhydroquinone dimethyl ether was investigated using geometry minimization (ab initio and DFT) and NOE spectroscopic measurements. The theoretical and experimental results were consistent with the indirect participation of the aromatic methyl group in blocking the electrophile attack at position 3 of the aromatic ring. © 2011 Elsevier Ltd. All rights reserved.
publishDate 2011
dc.date.issued.fl_str_mv 2011
dc.date.accessioned.fl_str_mv 2020-05-31T18:05:42Z
dc.date.available.fl_str_mv 2020-05-31T18:05:42Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv https://repositorio.inpa.gov.br/handle/1/16205
dc.identifier.doi.none.fl_str_mv 10.1016/j.tetlet.2011.01.130
url https://repositorio.inpa.gov.br/handle/1/16205
identifier_str_mv 10.1016/j.tetlet.2011.01.130
dc.language.iso.fl_str_mv eng
language eng
dc.relation.ispartof.pt_BR.fl_str_mv Volume 52, Número 14, Pags. 1612-1614
dc.rights.driver.fl_str_mv Attribution-NonCommercial-NoDerivs 3.0 Brazil
http://creativecommons.org/licenses/by-nc-nd/3.0/br/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution-NonCommercial-NoDerivs 3.0 Brazil
http://creativecommons.org/licenses/by-nc-nd/3.0/br/
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Tetrahedron Letters
publisher.none.fl_str_mv Tetrahedron Letters
dc.source.none.fl_str_mv reponame:Repositório Institucional do INPA
instname:Instituto Nacional de Pesquisas da Amazônia (INPA)
instacron:INPA
instname_str Instituto Nacional de Pesquisas da Amazônia (INPA)
instacron_str INPA
institution INPA
reponame_str Repositório Institucional do INPA
collection Repositório Institucional do INPA
bitstream.url.fl_str_mv https://repositorio.inpa.gov.br/bitstream/1/16205/1/artigo-inpa.pdf
bitstream.checksum.fl_str_mv a75cdb593f5ae24bdd4953db285299a9
bitstream.checksumAlgorithm.fl_str_mv MD5
repository.name.fl_str_mv Repositório Institucional do INPA - Instituto Nacional de Pesquisas da Amazônia (INPA)
repository.mail.fl_str_mv
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