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Abstract:

Irradiation of triphenylamine (Ph3N) in nitrogen-flushed solution leads to 9-phenylcarbazole and two tetrahydroderivatives (1,2,3,4- and 1,2,7,8-) via disproportionation of the corresponding 4a,4b-dihydrocarbazole. In oxygen-equilibrated solution oxidative cyclization occurs through the intermediacy of a triplet peroxy diradical, which either abstracts a hydrogen atom intramolecularly or (mainly) cleaves back to the reagents. The role of the key intermediates is supported by DFT calculations and by trapping by triarylphosphines (that are thus efficiently oxidized, while preventing the cyclization of Ph3N). The hydroperoxide, on the other hand, causes inefficient co-oxidation of sulfides. © 2014 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:(Co)oxidation/cyclization processes upon irradiation of triphenylamine
Autor:Bonesi, S.M.; Dondi, D.; Protti, S.; Fagnoni, M.; Albini, A.
Filiación:PhotoGreen Lab, Department of Chemistry, University of Pavia, V. Le Taramelli 12, 27100 Pavia, Italy
CIHIDECAR-CONICET, Department of Organic Chemistry, FCEyN University of Buenos Aires, 3er Piso, Pabellón 2, Ciudad Universitaria, CP1428 Buenos Aires, Argentina
Palabras clave:Phosphine oxidation; Photocyclization of triphenylamine; Photooxidation; Sulfide oxidation; amine; hydrogen; hydroperoxide; triphenylamine; unclassified drug; article; calculation; cooxidation; cyclization; density functional theory; irradiation; oxidation; photooxidation
Año:2014
Volumen:55
Número:18
Página de inicio:2932
Página de fin:2935
DOI: http://dx.doi.org/10.1016/j.tetlet.2014.03.086
Título revista:Tetrahedron Letters
Título revista abreviado:Tetrahedron Lett.
ISSN:00404039
CODEN:TELEA
CAS:hydrogen, 12385-13-6, 1333-74-0
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v55_n18_p2932_Bonesi

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Citas:

---------- APA ----------
Bonesi, S.M., Dondi, D., Protti, S., Fagnoni, M. & Albini, A. (2014) . (Co)oxidation/cyclization processes upon irradiation of triphenylamine. Tetrahedron Letters, 55(18), 2932-2935.
http://dx.doi.org/10.1016/j.tetlet.2014.03.086
---------- CHICAGO ----------
Bonesi, S.M., Dondi, D., Protti, S., Fagnoni, M., Albini, A. "(Co)oxidation/cyclization processes upon irradiation of triphenylamine" . Tetrahedron Letters 55, no. 18 (2014) : 2932-2935.
http://dx.doi.org/10.1016/j.tetlet.2014.03.086
---------- MLA ----------
Bonesi, S.M., Dondi, D., Protti, S., Fagnoni, M., Albini, A. "(Co)oxidation/cyclization processes upon irradiation of triphenylamine" . Tetrahedron Letters, vol. 55, no. 18, 2014, pp. 2932-2935.
http://dx.doi.org/10.1016/j.tetlet.2014.03.086
---------- VANCOUVER ----------
Bonesi, S.M., Dondi, D., Protti, S., Fagnoni, M., Albini, A. (Co)oxidation/cyclization processes upon irradiation of triphenylamine. Tetrahedron Lett. 2014;55(18):2932-2935.
http://dx.doi.org/10.1016/j.tetlet.2014.03.086