On the Reaction of 1,3-Diphenylisobenzofuran and (2-Iodoethynyl)(phenyl)iodonium Triflate. A Unique Case of Oxygen Transfer from the Diels-Alder Adduct to the Diene

Reaction of 1,3-diphenylisobenzofuran (DPIBF) with 2-(iodoethynyl)(phenyl)- iodonium triflate at room temperature gave the expected Diels-Alder adduct, but using an excess of DFIBF (2 equiv.) and performing the reaction at 55 °C or heating at this temperature during the concentration stage, the init...

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Autores: Camps García, Pelayo, Gómez Nadal, Tània, Lozano Mena, David, Calvet Pallàs, Maria Teresa, Font Bardia, Ma. Mercedes
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2012
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/152534
Acceso en línea:https://hdl.handle.net/2445/152534
Access Level:acceso abierto
Palabra clave:Espectroscòpia de ressonància magnètica nuclear
Difracció de raigs X
Nuclear magnetic resonance spectroscopy
X-rays diffraction
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spelling On the Reaction of 1,3-Diphenylisobenzofuran and (2-Iodoethynyl)(phenyl)iodonium Triflate. A Unique Case of Oxygen Transfer from the Diels-Alder Adduct to the DieneCamps García, PelayoGómez Nadal, TàniaLozano Mena, DavidCalvet Pallàs, Maria TeresaFont Bardia, Ma. MercedesEspectroscòpia de ressonància magnètica nuclearDifracció de raigs XNuclear magnetic resonance spectroscopyX-rays diffractionReaction of 1,3-diphenylisobenzofuran (DPIBF) with 2-(iodoethynyl)(phenyl)- iodonium triflate at room temperature gave the expected Diels-Alder adduct, but using an excess of DFIBF (2 equiv.) and performing the reaction at 55 °C or heating at this temperature during the concentration stage, the initial orange solution or product mixture became dark brown and the products 1,2-phenylene-1,2-bis(phenylmethanone) and 2-(3-iodo-1,4-diphenylnaphthyl)(phenyl)iodonium triflate were obtained, which suggests an oxygen transfer between DPIBF and the initial adduct.MDPI2012info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://hdl.handle.net/2445/152534Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésReproducció del document publicat a: https://doi.org/10.3390/molecules17088795Molecules, 2012, vol. 17, num. 8, p. 8795-8803https://doi.org/10.3390/molecules17088795cc-by (c) Camps García, Pelayo et al., 2012http://creativecommons.org/licenses/by/3.0/esinfo:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/1525342026-05-27T06:46:51Z
dc.title.none.fl_str_mv On the Reaction of 1,3-Diphenylisobenzofuran and (2-Iodoethynyl)(phenyl)iodonium Triflate. A Unique Case of Oxygen Transfer from the Diels-Alder Adduct to the Diene
title On the Reaction of 1,3-Diphenylisobenzofuran and (2-Iodoethynyl)(phenyl)iodonium Triflate. A Unique Case of Oxygen Transfer from the Diels-Alder Adduct to the Diene
spellingShingle On the Reaction of 1,3-Diphenylisobenzofuran and (2-Iodoethynyl)(phenyl)iodonium Triflate. A Unique Case of Oxygen Transfer from the Diels-Alder Adduct to the Diene
Camps García, Pelayo
Espectroscòpia de ressonància magnètica nuclear
Difracció de raigs X
Nuclear magnetic resonance spectroscopy
X-rays diffraction
title_short On the Reaction of 1,3-Diphenylisobenzofuran and (2-Iodoethynyl)(phenyl)iodonium Triflate. A Unique Case of Oxygen Transfer from the Diels-Alder Adduct to the Diene
title_full On the Reaction of 1,3-Diphenylisobenzofuran and (2-Iodoethynyl)(phenyl)iodonium Triflate. A Unique Case of Oxygen Transfer from the Diels-Alder Adduct to the Diene
title_fullStr On the Reaction of 1,3-Diphenylisobenzofuran and (2-Iodoethynyl)(phenyl)iodonium Triflate. A Unique Case of Oxygen Transfer from the Diels-Alder Adduct to the Diene
title_full_unstemmed On the Reaction of 1,3-Diphenylisobenzofuran and (2-Iodoethynyl)(phenyl)iodonium Triflate. A Unique Case of Oxygen Transfer from the Diels-Alder Adduct to the Diene
title_sort On the Reaction of 1,3-Diphenylisobenzofuran and (2-Iodoethynyl)(phenyl)iodonium Triflate. A Unique Case of Oxygen Transfer from the Diels-Alder Adduct to the Diene
dc.creator.none.fl_str_mv Camps García, Pelayo
Gómez Nadal, Tània
Lozano Mena, David
Calvet Pallàs, Maria Teresa
Font Bardia, Ma. Mercedes
author Camps García, Pelayo
author_facet Camps García, Pelayo
Gómez Nadal, Tània
Lozano Mena, David
Calvet Pallàs, Maria Teresa
Font Bardia, Ma. Mercedes
author_role author
author2 Gómez Nadal, Tània
Lozano Mena, David
Calvet Pallàs, Maria Teresa
Font Bardia, Ma. Mercedes
author2_role author
author
author
author
dc.subject.none.fl_str_mv Espectroscòpia de ressonància magnètica nuclear
Difracció de raigs X
Nuclear magnetic resonance spectroscopy
X-rays diffraction
topic Espectroscòpia de ressonància magnètica nuclear
Difracció de raigs X
Nuclear magnetic resonance spectroscopy
X-rays diffraction
description Reaction of 1,3-diphenylisobenzofuran (DPIBF) with 2-(iodoethynyl)(phenyl)- iodonium triflate at room temperature gave the expected Diels-Alder adduct, but using an excess of DFIBF (2 equiv.) and performing the reaction at 55 °C or heating at this temperature during the concentration stage, the initial orange solution or product mixture became dark brown and the products 1,2-phenylene-1,2-bis(phenylmethanone) and 2-(3-iodo-1,4-diphenylnaphthyl)(phenyl)iodonium triflate were obtained, which suggests an oxygen transfer between DPIBF and the initial adduct.
publishDate 2012
dc.date.none.fl_str_mv 2012
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/152534
url https://hdl.handle.net/2445/152534
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Reproducció del document publicat a: https://doi.org/10.3390/molecules17088795
Molecules, 2012, vol. 17, num. 8, p. 8795-8803
https://doi.org/10.3390/molecules17088795
dc.rights.none.fl_str_mv cc-by (c) Camps García, Pelayo et al., 2012
http://creativecommons.org/licenses/by/3.0/es
info:eu-repo/semantics/openAccess
rights_invalid_str_mv cc-by (c) Camps García, Pelayo et al., 2012
http://creativecommons.org/licenses/by/3.0/es
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv MDPI
publisher.none.fl_str_mv MDPI
dc.source.none.fl_str_mv Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
reponame:Dipòsit Digital de la UB
instname:Universidad de Barcelona
instname_str Universidad de Barcelona
reponame_str Dipòsit Digital de la UB
collection Dipòsit Digital de la UB
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,301629

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