Photosensitized oxidation of sulfides: Discriminating between the singlet-oxygen mechanism and electron transfer involving superoxide anion or molecular oxygen

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The oxidation of diethyl and diphenyl sulfide photosensitized by dicyanoanthracene (DCA), N-methylquinolinium tetrafluoroborate (NMQ +), and triphenylpyrylium tetrafluoroborate (TPP+) has been explored by steady-state and laser flash photolysis studies in acetonitrile, methanol, and 1,2-dichloroetha...

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Autor principal: Bonesi, S.M
Otros Autores: Manet, I., Freccero, M., Fagnoni, M., Albini, A.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2006
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100 1 |a Bonesi, S.M. 
245 1 0 |a Photosensitized oxidation of sulfides: Discriminating between the singlet-oxygen mechanism and electron transfer involving superoxide anion or molecular oxygen 
260 |c 2006 
270 1 0 |m Albini, A.; Dept. Org. Chem., University of Pavia, v. Taramelli 10, 27100 Pavia, Italy; email: angelo.albini@unipv.it 
506 |2 openaire  |e Política editorial 
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520 3 |a The oxidation of diethyl and diphenyl sulfide photosensitized by dicyanoanthracene (DCA), N-methylquinolinium tetrafluoroborate (NMQ +), and triphenylpyrylium tetrafluoroborate (TPP+) has been explored by steady-state and laser flash photolysis studies in acetonitrile, methanol, and 1,2-dichloroethane. In the Et2S/DCA system sulfide-enhanced intersystem crossing leads to generation of 1O2, which eventually gives the sulfoxide via a persulfoxide ; this mechanism plays no role with Ph2S, though enhanced formation of 3DCA has been demonstrated. In all other cases an electron-transfer (ET) mechanism is involved. Electron-transfer sulfoxidation occurs with efficiency essentially independent of the sulfide structure, is subject to quenching by benzoquinone, and does not lead to Ph2SO cooxidation. Formation of the radical cations R2S.+ has been assessed by flash photolysis (medium-dependent yield, dichloroethane ≫ CH3CN > CH3OH) and confirmed by quenching with 1,4-dimethoxybenzene. Electron-transfer oxidations occur both when the superoxide anion is generated by the reduced sensitizer (DCA.-, NMQ.) and when this is not the case (TPP.). Although it is possible that different mechanisms op erate with different ET sensitizers, a plausible unitary mechanism can be proposed. This considers that reaction between R2S.+ and O2.- mainly involves back electron transfer, whereas sulfoxidation results primarily from the reaction of the sulfide radical cation with molecular oxygen. Calculations indeed show that the initially formed fleeting complex RS2 +⋯O-O. adds to a sulfide molecule and gives strongly stabilized R2S-O.-+O-SR2 via an accessible transition state. This intermediate gives the sulfoxide, probably via a radical cation chain path. This mechanism explains the larger scope of ET sulfoxidation with respect to the singlet-oxygen process. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.  |l eng 
593 |a CHIDECAR-CONICET, Dep. Quim. Org., Ciudad Universidaria, 1428 Buenos Aires, Argentina 
593 |a Dept. Org. Chem., University of Pavia, v. Taramelli 10, 27100 Pavia, Italy 
593 |a ISOF-CNR, via P. Gobetti 101, 40129 Bologna, Italy 
690 1 0 |a ELECTRON TRANSFER OXIDATION 
690 1 0 |a PHOTOCHEMISTRY REACTION MECHANISMS 
690 1 0 |a SULFIDES 
690 1 0 |a ACETONITRILE 
690 1 0 |a ELECTRON TRANSITIONS 
690 1 0 |a NEGATIVE IONS 
690 1 0 |a PHOTOLYSIS 
690 1 0 |a PHOTOSENSITIVITY 
690 1 0 |a QUENCHING 
690 1 0 |a ELECTRON TRANSFER OXIDATION 
690 1 0 |a PHOTOCHEMISTRY REACTION MECHANISMS 
690 1 0 |a SULFIDES 
690 1 0 |a SULFOXIDATION 
690 1 0 |a SULFUR COMPOUNDS 
700 1 |a Manet, I. 
700 1 |a Freccero, M. 
700 1 |a Fagnoni, M. 
700 1 |a Albini, A. 
773 0 |d 2006  |g v. 12  |h pp. 4844-4857  |k n. 18  |p Chem. Eur. J.  |x 09476539  |w (AR-BaUEN)CENRE-83  |t Chemistry - A European Journal 
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856 4 0 |u https://doi.org/10.1002/chem.200501144  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_09476539_v12_n18_p4844_Bonesi  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09476539_v12_n18_p4844_Bonesi  |y Registro en la Biblioteca Digital 
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