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Abstract:

The direct irradiation of diphenyl sulfide and p-substituted thioanisoles in the presence of oxygen was investigated by means of both steady state and laser flash photolysis experiments. Two competitive pathways took place from the triplet excited state of thioanisoles, C-S bond cleavage, finally leading to aryl sulfinic acid and sensitized oxidation leading to S-oxidation. Co-oxidation of dodecyl methyl sulfide occurred efficiently implying that an S-persulfoxide intermediate is involved during the sensitized oxidation. On the other hand, triplet state of diphenyl sulfide also showed competitive C-S bond cleavage giving phenyl sulfinic acid and ionization to diphenyl sulfide radical cation that in turn led to diphenyl sulfoxide. The rate constants of the above reactions were determined by time-resolved experiments. © 2017 American Chemical Society.

Registro:

Documento: Artículo
Título:Direct Irradiaton of Aryl Sulfides: Homolytic Fragmentation and Sensitized S-Oxidation
Autor:Bonesi, S.M.; Crespi, S.; Merli, D.; Manet, I.; Albini, A.
Filiación:Departamento de Química Orgánica, CIHIDECAR, CONICET, Ciudad Universitaria, FCEyN, University of Buenos Aires, 3er Piso, Pabellón 2, Buenos Aires, 1428, Argentina
PhotoGreen Lab, Department of Chemistry, V.le Taramelli 12, Pavia, 27100, Italy
Department of Chemistry, V.le Taramelli 12, Pavia, 27100, Italy
ISOF-CNR, via Gobetti 101, Bologna, 40129, Italy
Palabras clave:Chemical bonds; Excited states; Oxidation; Photolysis; Rate constants; Sulfur compounds; C-S bond cleavage; Diphenyl sulfoxides; Direct irradiation; Dodecyl methyl sulfide; Laser flash photolysis; Radical cations; Sensitized oxidation; Time resolved experiments; Reaction intermediates; biphenyl; diphenyl sulfoxide; singlet oxygen; sulfoxide; unclassified drug; Article; chemical bond; chemical structure; electron transport; irradiation; photochemistry; photooxidation; quantum yield; steady state
Año:2017
Volumen:82
Número:17
Página de inicio:9054
Página de fin:9065
DOI: http://dx.doi.org/10.1021/acs.joc.7b01518
Título revista:Journal of Organic Chemistry
Título revista abreviado:J. Org. Chem.
ISSN:00223263
CODEN:JOCEA
CAS:biphenyl, 92-52-4; sulfoxide, 120-62-7
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v82_n17_p9054_Bonesi

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Citas:

---------- APA ----------
Bonesi, S.M., Crespi, S., Merli, D., Manet, I. & Albini, A. (2017) . Direct Irradiaton of Aryl Sulfides: Homolytic Fragmentation and Sensitized S-Oxidation. Journal of Organic Chemistry, 82(17), 9054-9065.
http://dx.doi.org/10.1021/acs.joc.7b01518
---------- CHICAGO ----------
Bonesi, S.M., Crespi, S., Merli, D., Manet, I., Albini, A. "Direct Irradiaton of Aryl Sulfides: Homolytic Fragmentation and Sensitized S-Oxidation" . Journal of Organic Chemistry 82, no. 17 (2017) : 9054-9065.
http://dx.doi.org/10.1021/acs.joc.7b01518
---------- MLA ----------
Bonesi, S.M., Crespi, S., Merli, D., Manet, I., Albini, A. "Direct Irradiaton of Aryl Sulfides: Homolytic Fragmentation and Sensitized S-Oxidation" . Journal of Organic Chemistry, vol. 82, no. 17, 2017, pp. 9054-9065.
http://dx.doi.org/10.1021/acs.joc.7b01518
---------- VANCOUVER ----------
Bonesi, S.M., Crespi, S., Merli, D., Manet, I., Albini, A. Direct Irradiaton of Aryl Sulfides: Homolytic Fragmentation and Sensitized S-Oxidation. J. Org. Chem. 2017;82(17):9054-9065.
http://dx.doi.org/10.1021/acs.joc.7b01518