Formation of 2,2-dimethylchroman-4-ones during the photoinduced rearrangement of some aryl 3-methyl-2-butenoate esters. A mechanistic insight

Several aryl 3-methyl-2-butenoate esters upon irradiation lead to the formation of [1,3]-migrated photoproducts, phenol and, surprisingly 2,2-dimethylchroman-4-one derivatives. The starting photochemical reaction takes place from the singlet excited state of the ester and as a total mechanism two co...

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Autores principales:	Iguchi, D., Erra-Balsells, R., Bonesi, S.M.
Formato:	JOUR
Materias:	2,2-Dimethylchroman-4-ones Aryl 3-methyl-2-butenoate esters oxa-Michael cyclization photo-Fries rearrangement Thermal 6π-electrocyclic reaction 2,2 dimethylchroman 4 one aryl 3 methyl 2 butenoate ester chroman derivative cyclohexane ester derivative unclassified drug Article chemical reaction cyclization photo fries rearrangement photochemistry priority journal reaction analysis
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_00404020_v72_n16_p1903_Iguchi
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	todo:paper_00404020_v72_n16_p1903_Iguchi
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spelling	todo:paper_00404020_v72_n16_p1903_Iguchi2023-10-03T14:50:46Z Formation of 2,2-dimethylchroman-4-ones during the photoinduced rearrangement of some aryl 3-methyl-2-butenoate esters. A mechanistic insight Iguchi, D. Erra-Balsells, R. Bonesi, S.M. 2,2-Dimethylchroman-4-ones Aryl 3-methyl-2-butenoate esters oxa-Michael cyclization photo-Fries rearrangement Thermal 6π-electrocyclic reaction 2,2 dimethylchroman 4 one aryl 3 methyl 2 butenoate ester chroman derivative cyclohexane ester derivative unclassified drug Article chemical reaction cyclization photo fries rearrangement photochemistry priority journal reaction analysis Several aryl 3-methyl-2-butenoate esters upon irradiation lead to the formation of [1,3]-migrated photoproducts, phenol and, surprisingly 2,2-dimethylchroman-4-one derivatives. The starting photochemical reaction takes place from the singlet excited state of the ester and as a total mechanism two consecutive reaction pathways are proposed. The former involves the photo-Fries rearrangement of the esters in all the solvents studied and, depending on the proticity of the solvent, the latter involves an ESIPT process followed by thermal 6π-electrocyclic reaction and/or thermal (intramolecular oxa-Michael addition) cyclization of the ortho regioisomers photoformed. This second pathway is responsible of the formation of the 2,2-dimethylchroman-4-one derivatives. © 2016 Elsevier Ltd. Fil:Erra-Balsells, R. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Bonesi, S.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00404020_v72_n16_p1903_Iguchi
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	2,2-Dimethylchroman-4-ones Aryl 3-methyl-2-butenoate esters oxa-Michael cyclization photo-Fries rearrangement Thermal 6π-electrocyclic reaction 2,2 dimethylchroman 4 one aryl 3 methyl 2 butenoate ester chroman derivative cyclohexane ester derivative unclassified drug Article chemical reaction cyclization photo fries rearrangement photochemistry priority journal reaction analysis
spellingShingle	2,2-Dimethylchroman-4-ones Aryl 3-methyl-2-butenoate esters oxa-Michael cyclization photo-Fries rearrangement Thermal 6π-electrocyclic reaction 2,2 dimethylchroman 4 one aryl 3 methyl 2 butenoate ester chroman derivative cyclohexane ester derivative unclassified drug Article chemical reaction cyclization photo fries rearrangement photochemistry priority journal reaction analysis Iguchi, D. Erra-Balsells, R. Bonesi, S.M. Formation of 2,2-dimethylchroman-4-ones during the photoinduced rearrangement of some aryl 3-methyl-2-butenoate esters. A mechanistic insight
topic_facet	2,2-Dimethylchroman-4-ones Aryl 3-methyl-2-butenoate esters oxa-Michael cyclization photo-Fries rearrangement Thermal 6π-electrocyclic reaction 2,2 dimethylchroman 4 one aryl 3 methyl 2 butenoate ester chroman derivative cyclohexane ester derivative unclassified drug Article chemical reaction cyclization photo fries rearrangement photochemistry priority journal reaction analysis
description	Several aryl 3-methyl-2-butenoate esters upon irradiation lead to the formation of [1,3]-migrated photoproducts, phenol and, surprisingly 2,2-dimethylchroman-4-one derivatives. The starting photochemical reaction takes place from the singlet excited state of the ester and as a total mechanism two consecutive reaction pathways are proposed. The former involves the photo-Fries rearrangement of the esters in all the solvents studied and, depending on the proticity of the solvent, the latter involves an ESIPT process followed by thermal 6π-electrocyclic reaction and/or thermal (intramolecular oxa-Michael addition) cyclization of the ortho regioisomers photoformed. This second pathway is responsible of the formation of the 2,2-dimethylchroman-4-one derivatives. © 2016 Elsevier Ltd.
format	JOUR
author	Iguchi, D. Erra-Balsells, R. Bonesi, S.M.
author_facet	Iguchi, D. Erra-Balsells, R. Bonesi, S.M.
author_sort	Iguchi, D.
title	Formation of 2,2-dimethylchroman-4-ones during the photoinduced rearrangement of some aryl 3-methyl-2-butenoate esters. A mechanistic insight
title_short	Formation of 2,2-dimethylchroman-4-ones during the photoinduced rearrangement of some aryl 3-methyl-2-butenoate esters. A mechanistic insight
title_full	Formation of 2,2-dimethylchroman-4-ones during the photoinduced rearrangement of some aryl 3-methyl-2-butenoate esters. A mechanistic insight
title_fullStr	Formation of 2,2-dimethylchroman-4-ones during the photoinduced rearrangement of some aryl 3-methyl-2-butenoate esters. A mechanistic insight
title_full_unstemmed	Formation of 2,2-dimethylchroman-4-ones during the photoinduced rearrangement of some aryl 3-methyl-2-butenoate esters. A mechanistic insight
title_sort	formation of 2,2-dimethylchroman-4-ones during the photoinduced rearrangement of some aryl 3-methyl-2-butenoate esters. a mechanistic insight
url	http://hdl.handle.net/20.500.12110/paper_00404020_v72_n16_p1903_Iguchi
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_version_	1807316760857149440

Formation of 2,2-dimethylchroman-4-ones during the photoinduced rearrangement of some aryl 3-methyl-2-butenoate esters. A mechanistic insight

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