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Abstract:

Product distribution, total quenching rate (kT), and rate of chemical reaction (kr) with singlet oxygen have been determined for some alkyl, benzyl, α-methylbenzyl, and cumyl sulfides. Their contributions depend on the steric hindering around the sulfur atom. In protic solvents, the sulfoxide is the main product via a hydrogen-bonded persulfoxide. In apolar solvents, intramolecular α-H abstraction leads to oxidative C-S bond cleavage, with varying efficiency. The behavior of sulfides is compared to that of alkenes and amines. © 2006 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Reaction of singlet oxygen with some benzylic sulfides
Autor:Bonesi, S.M.; Fagnoni, M.; Monti, S.; Albini, A.
Filiación:CHIDECAR-CONICET, Dep. Quim. Org., Fac. Cien. Ex. Nat., Ciudad Universidaria, 1428 Buenos Aires, Argentina
Department of Organic Chemistry, University of Pavia, v. Taramelli 10, 27100 Pavia, Italy
ISOF-CNR Institute, v. Gobetti 123, 40129 Bologna, Italy
Palabras clave:alkene; alkyl group; amine; benzyl derivative; hydrogen; oxygen; sulfide; sulfoxide; sulfur; article; chemical bond; chemical reaction; priority journal
Año:2006
Volumen:62
Número:46
Página de inicio:10716
Página de fin:10723
DOI: http://dx.doi.org/10.1016/j.tet.2006.07.110
Título revista:Tetrahedron
Título revista abreviado:Tetrahedron
ISSN:00404020
CODEN:TETRA
CAS:hydrogen, 12385-13-6, 1333-74-0; oxygen, 7782-44-7; sulfide, 18496-25-8; sulfoxide, 120-62-7; sulfur, 13981-57-2, 7704-34-9
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v62_n46_p10716_Bonesi

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Citas:

---------- APA ----------
Bonesi, S.M., Fagnoni, M., Monti, S. & Albini, A. (2006) . Reaction of singlet oxygen with some benzylic sulfides. Tetrahedron, 62(46), 10716-10723.
http://dx.doi.org/10.1016/j.tet.2006.07.110
---------- CHICAGO ----------
Bonesi, S.M., Fagnoni, M., Monti, S., Albini, A. "Reaction of singlet oxygen with some benzylic sulfides" . Tetrahedron 62, no. 46 (2006) : 10716-10723.
http://dx.doi.org/10.1016/j.tet.2006.07.110
---------- MLA ----------
Bonesi, S.M., Fagnoni, M., Monti, S., Albini, A. "Reaction of singlet oxygen with some benzylic sulfides" . Tetrahedron, vol. 62, no. 46, 2006, pp. 10716-10723.
http://dx.doi.org/10.1016/j.tet.2006.07.110
---------- VANCOUVER ----------
Bonesi, S.M., Fagnoni, M., Monti, S., Albini, A. Reaction of singlet oxygen with some benzylic sulfides. Tetrahedron. 2006;62(46):10716-10723.
http://dx.doi.org/10.1016/j.tet.2006.07.110