Reaction of singlet oxygen with some benzylic sulfides

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...

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Detalles Bibliográficos
Autores principales: Bonesi, S.M., Fagnoni, M., Monti, S., Albini, A.
Formato: JOUR
Materias:
alkene
alkyl group
amine
benzyl derivative
hydrogen
oxygen
sulfide
sulfoxide
sulfur
article
chemical bond
chemical reaction
priority journal
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_00404020_v62_n46_p10716_Bonesi
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_00404020_v62_n46_p10716_Bonesi
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spelling todo:paper_00404020_v62_n46_p10716_Bonesi2023-10-03T14:50:43Z Reaction of singlet oxygen with some benzylic sulfides Bonesi, S.M. Fagnoni, M. Monti, S. Albini, A. alkene alkyl group amine benzyl derivative hydrogen oxygen sulfide sulfoxide sulfur article chemical bond chemical reaction priority journal 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00404020_v62_n46_p10716_Bonesi
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic alkene
alkyl group
amine
benzyl derivative
hydrogen
oxygen
sulfide
sulfoxide
sulfur
article
chemical bond
chemical reaction
priority journal
spellingShingle alkene
alkyl group
amine
benzyl derivative
hydrogen
oxygen
sulfide
sulfoxide
sulfur
article
chemical bond
chemical reaction
priority journal
Bonesi, S.M.
Fagnoni, M.
Monti, S.
Albini, A.
Reaction of singlet oxygen with some benzylic sulfides
topic_facet alkene
alkyl group
amine
benzyl derivative
hydrogen
oxygen
sulfide
sulfoxide
sulfur
article
chemical bond
chemical reaction
priority journal
description 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.
format JOUR
author Bonesi, S.M.
Fagnoni, M.
Monti, S.
Albini, A.
author_facet Bonesi, S.M.
Fagnoni, M.
Monti, S.
Albini, A.
author_sort Bonesi, S.M.
title Reaction of singlet oxygen with some benzylic sulfides
title_short Reaction of singlet oxygen with some benzylic sulfides
title_full Reaction of singlet oxygen with some benzylic sulfides
title_fullStr Reaction of singlet oxygen with some benzylic sulfides
title_full_unstemmed Reaction of singlet oxygen with some benzylic sulfides
title_sort reaction of singlet oxygen with some benzylic sulfides
url http://hdl.handle.net/20.500.12110/paper_00404020_v62_n46_p10716_Bonesi
work_keys_str_mv AT bonesism reactionofsingletoxygenwithsomebenzylicsulfides
AT fagnonim reactionofsingletoxygenwithsomebenzylicsulfides
AT montis reactionofsingletoxygenwithsomebenzylicsulfides
AT albinia reactionofsingletoxygenwithsomebenzylicsulfides
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