Photo-oxidation of di-n-butylsulfide by various electron transfer sensitizers in oxygenated acetonitrile

Photochemical and Photobiological Sciences

Volumn 4, Issue 2, 2005, Pages 221-229

  Latour, Virginie ^a   Pigot, Thierry ^a   Simon, Maryse ^a   Cardy, Henri ^a   Lacombe, Sylvie ^a  

^a UNIVERSITÉ DE PAU ET DES PAYS DE L'ADOUR   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ANION; ANTHRACENE DERIVATIVE; ANTHRAQUINONE; BENZENE DERIVATIVE; BENZOIC ACID DERIVATIVE; BENZOPHENONE DERIVATIVE; BORIC ACID; CHLORANIL; CYANIC ACID DERIVATIVE; DI N BUTYLSULFIDE; FLUORINE DERIVATIVE; PEROXY RADICAL; PHENYL GROUP; PHOTOSENSITIZING AGENT; QUINONE DERIVATIVE; ROSE BENGAL; SINGLET OXYGEN; SULFIDE; SULFUR DERIVATIVE; SULFURIC ACID; SUPEROXIDE; TITANIUM DIOXIDE; UNCLASSIFIED DRUG;

ARTICLE; BLEACHING; COMPARATIVE STUDY; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; ELECTRON TRANSPORT; EXPERIMENTATION; IRRADIATION; OXYGENATION; PHOTOOXIDATION; PHOTOSENSITIZATION; PRIORITY JOURNAL;

EID: 14644399268     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b413865c     Document Type: Article

References (64)

1. W. Ando Photo-oxidation of organosulfur compounds Sulfur Rep. 1981 1 147-213.
2. J. J. Liang C. L. Gu M. L. Kacher C. S. Foote Chemistry of singlet oxygen. 45 Mechanism of the photo-oxidation of sulfides J. Am. Chem. Soc. 1983 105 4717-4721.
3. E. L. Clennan The reactions of sulfides and sulfenic acid derivatives with singlet oxygen Sulfur Rep. 1996 19 171-214.
4. E. L. Clennan Persulfoxide: key intermediate in reactions of singlet oxygen with sulfides Acc. Chem. Res. 2001 34 878-884.
5. J. Eriksen C. S. Foote T. L. Parker Photosensitized oxygenation of alkenes and sulfides via a non-singlet oxygen mechanism J. Am. Chem. Soc. 1977 99 6455-6456.
6. E. Baciocchi C. Crescenzi O. Lanzalunga Photoinduced electron transfer reactions of benzyl phenyl sulfides promoted by 9,10-dicyanoanthracene Tetrahedron 1997 53 4469-4478.
7. Y. Shiraishi Y. Taki T. Hirai I. Komasawa Visible light-induced desulfurization technique for light oil Chem. Commun. 1998 2601-2602.
8. W. Ando T. Nagashima K. Saito S. Kohmoto Dye- and dicyanoanthracene-photosensitized oxygenations of sulfur compounds. Product selectivity J. Chem. Soc., Chem. Commun. 1979 154-156.
9. N. Soggiu H. Cardy J. L. Habib-Jiwan I. Leray J. Ph. Soumillion S. Lacombe Organic sulfide photo-oxidation using sensitizers covalently grafted on silica: towards a more efficient and selective photochemistry J. Photochem. Photobiol. A: Chem. 1999 124 1-8.
10. B. L. Miller T. D. Williams C. Schöneich Mechanism of sulfoxide formation through reaction of sulfur radical cation complexes with superoxide or hydroxide ion in oxygenated aqueous solution J. Am. Chem. Soc. 1996 118 11014-11025.
11. B. Marciniak K. Bobrowski G. L. Hug Quenching of triplet states of aromatic ketones by sulfur-containing amino-acids in solution. Evidence for electron transfer J. Phys. Chem. 1993 97 11937-11943.
12. J. Guttenplan S. G. Cohen Aliphatic sulfides: physical quenchers and photoreducing agents J. Chem. Soc. D: Chem. Commun. 1969 247-248.
13. S. Inbar H. Linschitz S. G. Cohen Quenching and radical formation in the reaction of photoexcited benzophenone with thiols and thioethers. Nanosecond flash study J. Am. Chem. Soc. 1982 104 1679-1682.
14. S. Lacombe H. Cardy M. Simon A. Khoukh J. Ph. Soumillion M. Ayadim Oxidation of sulfides and disulfides under electron transfer or singlet oxygen photosensization using soluble or grafted sensitizers Photochem. Photobiol. Sci. 2002 1 347-354.
15. E. Baciocchi T. Del Giacco F. Elisei M. Gerini M. Guerra A. Lapi P. Liberali Electron transfer and singlet oxygen mechanisms in the photooxygenation of dibutyl sulfide and thioanisole in MeCN sensitized by N-methylquinolinium tetrafluoroborate and 9,10-dicyanoanthracene. The probable involvement of a thiadioxirane intermediate in electron transfer photooxygenations J. Am. Chem. Soc. 2003 125 16444-16454.
16. T. Tobien H. Hungerbühler K. D. Asmus Free radical and electrochemically induced oxidation of organic sulfur-, selenium- and phosphorus-compounds Phosphorus, Sulfur Silicon Relat. Elem. 1994 95–96 249-263.
17. M. L. Kacher C. S. Foote Chemistry of singlet oxygen: steric and electronic effects on the reactivity of sulfides with singlet oxygen Photochem. Photobiol. 1979 29 765-769.
18. G. Jones B. Huang Photoinduced electron-transfer for high potential quinone sensitizers and thianthrenes Tetrahedron Lett. 1993 269-272.
19. H. D. Roth M. Schilling Photoinduced electron transfer reactions. Radical cations of 1,2-diphenycyclopropane J. Am. Chem. Soc. 1980 102 7956-7958.
20. E. Hasegawa S. Koshii T. Horaguchi T. Shimizu Photoinduced electron transfer reactions of 1-substituted 2,3-diphenylaziridines with 9,10-dicyanoanthracene and chloranil J. Org. Chem. 1992 57 6342-6344.
21. K. Gollnick S. Held Hydroxyanthraquinones as sensitizers of electron-transfer-induced photooxygenation reactions J. Photochem. Photobiol. A: Chem. 1993 70 135-145.
22. +) during oxygen quenching of nπ* triplet phenyl ketones J. Phys. Chem. A 2002 106 228-235.
23. C. Schweitzer Z. Mehrad A. Noll E.-W. Grabner R. Schmidt Mechanism of photosensitized generation of singlet oxygen during oxygen quenching of triplet states J. Phys. Chem. A 2003 107 2192-2198.
24. C. Tanielan C. Schweitzer R. Seghrouchni M. Esch R. Mechin Polyoxometalate sensitization in mechanistic studies of photochemical reactions: the decatungstate anion as a reference sensitizer for photoinduced free radical oxygenations of organic compounds Photochem. Photobiol. Sci. 2003 2 297-305.
25. V. Latour, T. Pigot, P. Mocho, S. Blanc and S. Lacombe, Supported photosensitizers as new efficient materials for gas-phase photo-oxidation, Catal. Today, in press.
26. Technologie Photochimique, ed. A. Braun, M. T. Maurette and E. Oliveros, Presses Polytechniques Romandes, Lausanne, 1986, pp. 68–72.
27. A. Toutchkine D. Aebisher E. Clennan Substituent-dictated partitioning of intermediates on the sulfide singlet oxygen reaction surface. A new mechanism for oxidative C–S bond cleavage in α-hydroperoxysulfides J. Am. Chem. Soc. 2001 123 4966-4973.
28. R. Glass, Sulfur radical cations, in Topics in Current Chemistry, Springer-Verlag, Berlin, Heidelberg, 1999, pp. 2–87.
29. W. Adam J. Argüello A. Penenory Photochemical electron transfer reactions between sulfides and tetranitromethane. Oxidation vs. fragmentation of the sulfide radical-cation intermediate J. Org. Chem. 1998 63 3905-3910.
30. 2 J. Photochem. Photobiol. A: Chem. 1998 115 169-173.
31. D. Grosjean Photo-oxidation of methyl sulfide, ethyl sulfide and methanethiol Environ. Sci. Technol. 1984 18 460-468.
32. J. A. Howard, Homogeneous liquid-phase autooxidations, in Free Radicals, ed. J. K. Kochi, John Wiley, New York, 1973, vol. 2, pp. 3–62.
33. S. Jovanovic I. Jankovic L. Josimovic Electron-transfer reactions of alkylperoxy radicals J. Am. Chem. Soc. 1992 114 9018-9021.
34. J. K. Kochi, Oxygen radicals, in Free Radicals, ed. J. K. Kochi, John Wiley, New York, 1973, vol. 2, pp. 665–710.
35. J. Brocks H. D. Beckhaus A. Beckwith C. Rüchardt, Estimation of BDE and radical stabilization energies by ESR spectroscopy J. Org. Chem. 1998 63 1935-1943.
36. S. L. Murov, I. Carmichael and G. Hug, Handbook of Photochemistry, Marcel Dekker, New York, 2nd edn., 1993.
37. D. Barnard, L. Bateman, J. I. Cunnen, Oxidation of organic sulfides, in Inorganic Sulfur Compounds, ed. N. Kharash, Pergamon Press, New York, 1961, 229–257.
38. E. Robert-Banchereau S. Lacombe J. Ollivier Unsensitized photooxydation of sulfur compounds with molecular oxygen in solution Tetrahedron 1997 53 2087-2102.
39. R. Akaba H. Sakuragi K. Tokumaru Triphenylpyrylium-salt-sensitized electron transfer oxygenation of adamantylideneadamantane. Product fluorescence quenching and Laser Flash Photolysis studies J. Chem. Soc., Perkin Trans. 2 1991 291-297.
40. D. T. Sawyer, Activation of dioxygen species in biology, in Oxygen Complexes and Oxygen Activation by Transition Metals, ed. A. E. Martell and D. T. Sawyer, Plenum Press, New York, 1987, pp. 131–148.
41. C. Grewer H. D. Brauer Mechanism of the triplet-state quenching by molecular oxygen in solution J. Phys. Chem. 1994 98 4230-4235.
42. A. McLean M. Rodgers A variable temperature study of the quenching of benzophenone triplet by oxygen: involvement of exciplexes J. Am. Chem. Soc. 1992 114 3145-3147.
43. A. E. Alegria A. Ferrer G. Santiago E. Sepulveda W. Flores Photochemistry of water-soluble quinones. Production of hydroxyl radical, singlet oxygen and the superoxide anion J. Photochem. Photobiol. A: Chem. 1999 127 57-65.
44. A. Garner F. Willkinson Quenching of triplet states by molecular oxygen and the role of charge transfer interactions Chem. Phys. Lett. 1977 45 432-435.
45. D. C. Dobrowski P. Ogilby C. Foote Chemistry of singlet oxygen: 9,10-dicyanoanthracene sensitized formation of singlet oxygen J. Phys. Chem. 1983 87 2261-2263.
46. R. D. Scurlock P. R. Ogilby Production of singlet oxygen by 9,10-dicyanoanthracene and acridine: quantum yield in acetonitrile J. Photochem. Photobiol. A. Chem. 1993 72 1-7.
47. M. A. Fox, in Photocatalysis, fundamentals and applications, ed. N. Serpone and E. Pelizzetti, John Wiley and Sons, New York, 1989, pp. 421–455.
48. H. Al-Ekabi and N. Serpone, in Photocatalysis, fundamentals and applications, ed. N. Serpone and E. Pelizzetti, John Wiley and Sons, New York, 1989, pp. 457–488.
49. R. S. Davidson J. E. Pratt The titanium dioxide sensitized photo-oxidation of sulfides Tetrahedron Lett. 1983 24 5903-5906.
50. 2 mediated photocatalytic oxidation of thioethers Tetrahedron Lett. 1990 31 4533-4536.
51. 2 J. Photochem. Photobiol. A: Chem. 1998 115 169-173.
52. M. A. Fox Y. S. Kim A. Abdel-Wahab M. Dulay Photocatalytic decontamination of sulfur-containing alkyl halides on irradiated semi-conductor suspensions Catal. Lett. 1990 5 369-376.
53. S. Silverman C. Foote Singlet oxygen and electron transfer mechanisms in the dicyanoanthracene-sensitized photo-oxidation of 2,3-diphenyl-1,4-dioxene J. Am. Chem. Soc. 1991 113 7672-7675.
54. F. Willkinson W. Helman A. Ross Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation J. Phys. Chem. Ref. Data 1995 24 663-1021.
55. 2˙- by benzoquinone in cyanoaromatic-sensitized photooxygenations Tetrahedron Lett. 1984 25 2523-2526.
56. A. P. Schaap L. Lopez S. Anderson S. Gagnon Cosensitization by 9,10-dicyanoanthracene and biphenyl of the electron transfer photooxygenation of 1,1,2,2-tetraphenylcyclopropane Tetrahedron Lett. 1982 23 5493-5496.
57. K. Bobrowski B. Marciniak G. Hug A reinvestigation of the mechanism of photoreduction of benzophenones by alkylsulfides J. Photochem. Photobiol. A: Chem. 1994 81 159-168.
58. M. Miranda H. Garcia 2,4,6-triphenylpyrylium salt tetrafluoroborate as an electron-transfer sensitizer Chem. Rev. 1994 94 1063-1089.
59. R. Akaba S. Aihara S. Sakuragi K. Tokumaru Triphenylpyrylium salt as sensitizer for electron transfer oxygenation not involving superoxide anion J. Chem. Soc., Chem. Commun. 1987 1262-1263.
60. T. Del Giacco L. Lipparoni M. Ranchella C. Rol G. Sebastiani Mechanism of the oxidation of benzylic ethers photosensitized by a 2,4,6-triphenylpyrylium salt J. Chem. Soc., Perkin Trans. 2 2001 1802-1807.
61. Values between −0.94 V 61 and −0.78 V 62 may be found in the literature for the oxygen reduction potential.
62. J. Eriksen C. S. Foote Electron transfer photooxygenation. 5. Oxidation of phenyl-substituted alkenes sensitized by cyanoanthracenes J. Am. Chem. Soc. 1980 102 6083-6088.
63. G. J. Kavarnos N. J. Turro Photosensitization by reversible electron-transfer: theories, experimental evidence and examples Chem. Rev. 1986 86 401-449.
64. H. Ikeda K. Akiyama Y. Takahashi T. Nakamura S. Ishizaki Y. Shiratori H. Ohaku J. Goodman A. Houmam D. Wayner S. Tero-Kubota T. Miyashi Spectroscopic and calorimetric studies on the mechanism of methylenecyclopropane rearrangements triggererd by Photoinduced Electron Transfer J. Am. Chem. Soc. 2003 125 9145-9157.