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
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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
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Palabras clave: | alkene; alkyl group; amine; benzyl derivative; hydrogen; oxygen; sulfide; sulfoxide; sulfur; article; chemical bond; chemical reaction; priority journal |
Año: | 2006
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Volumen: | 62
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Número: | 46
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Página de inicio: | 10716
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Página de fin: | 10723
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DOI: |
http://dx.doi.org/10.1016/j.tet.2006.07.110 |
Título revista: | Tetrahedron
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Título revista abreviado: | Tetrahedron
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ISSN: | 00404020
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CODEN: | TETRA
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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
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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