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Abstract:

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.

Registro:

Documento: Artículo
Título:Formation of 2,2-dimethylchroman-4-ones during the photoinduced rearrangement of some aryl 3-methyl-2-butenoate esters. A mechanistic insight
Autor:Iguchi, D.; Erra-Balsells, R.; Bonesi, S.M.
Filiación:CIHIDECAR - CONICET, Departamento de Química Orgánica, FCEyN, University of Buenos Aires, 3erPiso Ciudad Universitaria, Pabellón 2, Buenos Aires, 1428, Argentina
Palabras clave: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
Año:2016
Volumen:72
Número:16
Página de inicio:1903
Página de fin:1910
DOI: http://dx.doi.org/10.1016/j.tet.2016.02.039
Título revista:Tetrahedron
Título revista abreviado:Tetrahedron
ISSN:00404020
CODEN:TETRA
CAS:cyclohexane, 110-82-7
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v72_n16_p1903_Iguchi

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Citas:

---------- APA ----------
Iguchi, D., Erra-Balsells, R. & Bonesi, S.M. (2016) . Formation of 2,2-dimethylchroman-4-ones during the photoinduced rearrangement of some aryl 3-methyl-2-butenoate esters. A mechanistic insight. Tetrahedron, 72(16), 1903-1910.
http://dx.doi.org/10.1016/j.tet.2016.02.039
---------- CHICAGO ----------
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" . Tetrahedron 72, no. 16 (2016) : 1903-1910.
http://dx.doi.org/10.1016/j.tet.2016.02.039
---------- MLA ----------
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" . Tetrahedron, vol. 72, no. 16, 2016, pp. 1903-1910.
http://dx.doi.org/10.1016/j.tet.2016.02.039
---------- VANCOUVER ----------
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. Tetrahedron. 2016;72(16):1903-1910.
http://dx.doi.org/10.1016/j.tet.2016.02.039