Photochemical carbon-sulfur bond cleavage in some alkyl and benzyl sulfides

Irradiation (254 nm) of five alkyl and benzyl ethyl sulfides causes efficient (Φr 0.27-0.90) homolytic cleavage of the C-S bond. Of the resulting fragments, thiyl radicals mainly couple, while alkyl radicals abstract hydrogen, disproportionate or couple when stabilized (benzyl). Selective trapping o...

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Autores principales: Bonesi, S.M., Fagnoni, M., Dondi, D., Albini, A.
Formato: JOUR
Materias:
Cleavage
Photochemistry
Radicals
Sulfides
Thioethers
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_00201693_v360_n3_p1230_Bonesi
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
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spelling todo:paper_00201693_v360_n3_p1230_Bonesi2023-10-03T14:17:20Z Photochemical carbon-sulfur bond cleavage in some alkyl and benzyl sulfides Bonesi, S.M. Fagnoni, M. Dondi, D. Albini, A. Cleavage Photochemistry Radicals Sulfides Thioethers Irradiation (254 nm) of five alkyl and benzyl ethyl sulfides causes efficient (Φr 0.27-0.90) homolytic cleavage of the C-S bond. Of the resulting fragments, thiyl radicals mainly couple, while alkyl radicals abstract hydrogen, disproportionate or couple when stabilized (benzyl). Selective trapping of either of the two types of radicals occurs in the presence of nucleophilic (methyl vinyl ether and 1-hexene) and, respectively, electrophilic (acrylonitrile) alkenes. When an easily oxidized radical is formed, e.g. cumyl, secondary electron transfer leads to the corresponding cation. © 2006 Elsevier B.V. All rights reserved. Fil:Bonesi, S.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00201693_v360_n3_p1230_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 Cleavage
Photochemistry
Radicals
Sulfides
Thioethers
spellingShingle Cleavage
Photochemistry
Radicals
Sulfides
Thioethers
Bonesi, S.M.
Fagnoni, M.
Dondi, D.
Albini, A.
Photochemical carbon-sulfur bond cleavage in some alkyl and benzyl sulfides
topic_facet Cleavage
Photochemistry
Radicals
Sulfides
Thioethers
description Irradiation (254 nm) of five alkyl and benzyl ethyl sulfides causes efficient (Φr 0.27-0.90) homolytic cleavage of the C-S bond. Of the resulting fragments, thiyl radicals mainly couple, while alkyl radicals abstract hydrogen, disproportionate or couple when stabilized (benzyl). Selective trapping of either of the two types of radicals occurs in the presence of nucleophilic (methyl vinyl ether and 1-hexene) and, respectively, electrophilic (acrylonitrile) alkenes. When an easily oxidized radical is formed, e.g. cumyl, secondary electron transfer leads to the corresponding cation. © 2006 Elsevier B.V. All rights reserved.
format JOUR
author Bonesi, S.M.
Fagnoni, M.
Dondi, D.
Albini, A.
author_facet Bonesi, S.M.
Fagnoni, M.
Dondi, D.
Albini, A.
author_sort Bonesi, S.M.
title Photochemical carbon-sulfur bond cleavage in some alkyl and benzyl sulfides
title_short Photochemical carbon-sulfur bond cleavage in some alkyl and benzyl sulfides
title_full Photochemical carbon-sulfur bond cleavage in some alkyl and benzyl sulfides
title_fullStr Photochemical carbon-sulfur bond cleavage in some alkyl and benzyl sulfides
title_full_unstemmed Photochemical carbon-sulfur bond cleavage in some alkyl and benzyl sulfides
title_sort photochemical carbon-sulfur bond cleavage in some alkyl and benzyl sulfides
url http://hdl.handle.net/20.500.12110/paper_00201693_v360_n3_p1230_Bonesi
work_keys_str_mv AT bonesism photochemicalcarbonsulfurbondcleavageinsomealkylandbenzylsulfides
AT fagnonim photochemicalcarbonsulfurbondcleavageinsomealkylandbenzylsulfides
AT dondid photochemicalcarbonsulfurbondcleavageinsomealkylandbenzylsulfides
AT albinia photochemicalcarbonsulfurbondcleavageinsomealkylandbenzylsulfides
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