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Abstract:

Systematic studies on the photo-Fries rearrangement of different 9H-carbazol-2-yl sulfonates 2 have shown that this type of conversion can be readily used for the preparative-scale introduction of alkyl- or arylsulfonyl groups into polycyclic aromatic compounds under very mild conditions. A series of new 1-sulfonyl- (3) or 3-sulfonyl-9H-carbazoles (4) were prepared in medium-to-good yields, and characterized by UV/VIS, 1H-NMR, and 13C-NMR spectroscopy, as well as by elemental analysis. Effects of irradiation wavelength, solvent polarity, presence or absence of O2, and photosensitizers were studied in detail. © 2006 Verlag Helvetica Chimica Acta AG.

Registro:

Documento: Artículo
Título:Photo-Fries rearrangement of carbazol-2-yl sulfonates: Efficient tool for the introduction of sulfonyl groups into polycyclic aromatic compounds
Autor:Crevatín, L.K.; Bonesi, S.M.; Erra-Balsells, R.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428-Buenos Aires, Argentina
Palabras clave:Nuclear magnetic resonance spectroscopy; Photosensitizers; Polycyclic aromatic hydrocarbons; Solvents; Irradiation wavelength; Photo-Fries; Solvent polarity; Organic compounds; 3 sulfonyl 9h carbazole derivative; 9h carbazol 2 yl sulfonate derivative; oxygen; photosensitizing agent; polycyclic aromatic compound; unclassified drug; article; irradiation; nuclear magnetic resonance spectroscopy; priority journal; ultraviolet spectroscopy; X ray photoelectron spectroscopy
Año:2006
Volumen:89
Número:6
Página de inicio:1147
Página de fin:1157
DOI: http://dx.doi.org/10.1002/hlca.200690112
Título revista:Helvetica Chimica Acta
Título revista abreviado:Helv. Chim. Acta
ISSN:0018019X
CODEN:HCACA
CAS:oxygen, 7782-44-7
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0018019X_v89_n6_p1147_Crevatin

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Citas:

---------- APA ----------
Crevatín, L.K., Bonesi, S.M. & Erra-Balsells, R. (2006) . Photo-Fries rearrangement of carbazol-2-yl sulfonates: Efficient tool for the introduction of sulfonyl groups into polycyclic aromatic compounds. Helvetica Chimica Acta, 89(6), 1147-1157.
http://dx.doi.org/10.1002/hlca.200690112
---------- CHICAGO ----------
Crevatín, L.K., Bonesi, S.M., Erra-Balsells, R. "Photo-Fries rearrangement of carbazol-2-yl sulfonates: Efficient tool for the introduction of sulfonyl groups into polycyclic aromatic compounds" . Helvetica Chimica Acta 89, no. 6 (2006) : 1147-1157.
http://dx.doi.org/10.1002/hlca.200690112
---------- MLA ----------
Crevatín, L.K., Bonesi, S.M., Erra-Balsells, R. "Photo-Fries rearrangement of carbazol-2-yl sulfonates: Efficient tool for the introduction of sulfonyl groups into polycyclic aromatic compounds" . Helvetica Chimica Acta, vol. 89, no. 6, 2006, pp. 1147-1157.
http://dx.doi.org/10.1002/hlca.200690112
---------- VANCOUVER ----------
Crevatín, L.K., Bonesi, S.M., Erra-Balsells, R. Photo-Fries rearrangement of carbazol-2-yl sulfonates: Efficient tool for the introduction of sulfonyl groups into polycyclic aromatic compounds. Helv. Chim. Acta. 2006;89(6):1147-1157.
http://dx.doi.org/10.1002/hlca.200690112