Photosensitized oxidation of phenyl and tert-butyl sulfides

Photochemical and Photobiological Sciences

Volumn 3, Issue 5, 2004, Pages 489-493

  Bonesi, Sergio M ^a   Fagnoni, Maurizio ^a   Monti, Sandra ^b   Albini, Angelo ^a  

^a UNIVERSITY OF PAVIA   (Italy)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; CARBOXYLIC ACID; METHANOL; OXYGEN; SINGLET OXYGEN; SULFIDE; SULFUR;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; OXIDATION; OXYGEN TRANSPORT; OXYGENATION; PHOTOCHEMICAL QUENCHING; PHOTOSENSITIZATION; PRIORITY JOURNAL; PROTON TRANSPORT; SULFOXIDATION;

EID: 3042699501     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b316891c     Document Type: Article

References (31)

1. E. L. Clennan Persulfoxide: key intermediate in reactions of singlet oxygen with sulfides Acc. Chem. Res. 2001 34 875-884.
2. E. L. Clennan The reactions of sulfides and sulfenic acid derivatives with singlet oxygen Sulfur Rep. 1996 19 171-214.
3. W. Ando Photooxidation of organosulfur compounds Sulfur Rep. 1981 1 147-213.
4. W. Ando and T. Takada, Photooxidation of sulfur compounds, in Singlet Oxygen, ed. A. A. Frimer, CRC, Boca Raton, FL, 1985, vol. 3, pp. 1–117.
5. F. Jensen, Theoretical aspects of the reactions of organic sulfur and phosphorous compounds with singlet oxygen, in Advances in Oxygenated Processes, ed. A. L. Baumstark, JAI Press, Greenwich, CT, 1995, vol. 4, pp. 1–48.
6. K. Ishiguro M. Hayashi Y. Sawaki Mechanism of sulfone formation in the reaction of sulfides and singlet oxygen: intermediacy of S-hydroperoxysulfonium ylide J. Am. Chem. Soc. 1996 118 7265-7271.
7. F. Wilkinson W. P. Helman A. B. Ross Rate constants for the decay and reactions of the lowest electronically excited state of molecular oxygen in solution. An expanded and revised compilation J. Phys. Chem. Ref. Data 1995 24 663-1021.
8. J. J. Liang C. L. Gu M. L. Kacher C. S. Foote Chemistry of singlet oxygen. 45. Mechanism of the photooxidation of sulfides J. Am. Chem. Soc. 1983 105 4717-4721.
9. 2-Ubertragung auf Schwefel-Verbindungen. Neuer Weg zu Sulfoxiden Angew. Chem. 1962 74 510.
10. M. L. Kacher C. S. Foote Chemistry of singlet oxygen - XXVIII. Steric and electronic effects on the reactivity of sulfides with singlet oxygen Photochem. Photobiol. 1979 29 765-769.
11. B. M. Monroe Rates of reaction of singlet oxygen with sulfides Photochem. Photobiol. 1979 29 761-764.
12. F. Jensen A Greer E. L. Clennan Reaction of organic sulfides with singlet oxygen. A revised mechanism J. Am. Chem. Soc. 1998 120 4439-4449.
13. M. L. McKee A theoretical study of unimolecular reactions of dimethyl persulfoxide J. Am. Chem. Soc. 1998 120 3963-3969.
14. E. L. Clennan H. Zhang Photooxidation of sulfenic acid derivatives.4. Reactions of singlet oxygen with sulfenamides J. Am. Chem. Soc. 1995 117 4218-4227.
15. E. L. Clennan M. F. Chen Photooxidations of sulfenic acid derivatives. 5. The reaction of singlet oxygen with ethyl phenyl sulfenate J. Org. Chem. 1995 60 6444-6447.
16. E. L. Clennan W. Zhou J. Chan Mechanistic organic chemistry in a microreactor. Zeolite controlled photooxidations of organic sulfides J. Org. Chem. 2002 67 9368-9378.
17. E. L. Clennan A. Greer Effect of alcohols on the photooxidative behavior of diethyl sulfide J. Org. Chem. 1996 61 4793-4797.
18. S. M. Bonesi A. Albini Effect of protic cosolvents on the photooxygenation of diethyl sulfide J. Org. Chem. 2000 65 4532-4536.
19. S. M. Bonesi M. Mella N. d’Alessandro G. G. Aloisi M. Vanossi A. Albini Photosensitized oxygenation of benzyl ethyl sulfide J. Org. Chem. 1998 9946-9955.
20. J. E. Frey T. Aiello D. N. Beaman H. Hutson S. R. Lang J. J. Puckett Charge-transfer complexes of tetracyanoethylene with alkyl and aryl derivatives of sulfur, selenium and tellurium J. Org. Chem. 1995 60 2891-2901.
21. W. Nakanishi S. Masuda T. Ishida K. Ohno Y. Harada Penning ionization electron spectroscopic of chalcogenides: PhOPh, PhSPh and PhSePh J. Org. Chem. 1989 54 540-544.
22. G. Wagner H. Bock Die Delokalisation von Schwefel-Elektronenpaaren in Alkylsulfiden und -disulfiden Chem. Ber. 1974 107 68-77.
23. M. S. Glass J. L. Broeker M. E. Jatcko Distinguishing ionization from sulfur p-type lone pair orbitals and carbon π-molecular orbitals by He I/He II photoelectron spectroscopy Tetrahedron 1989 45 1263-1272.
24. E. L. Clennan L. J. Noe E. Szneler T. Wen Hydrazines: new charge-transfer physical quenchers of singlet oxygen J. Am. Chem. Soc. 1990 112 5080-5085.
25. R. S. Davidson J. E. Pratt The titanium dioxide photooxidation of sulfides Tetrahedron Lett. 1983 24 5903-5906.
26. R. D. N. Rao M. C. R. Symons B. W. Won Radical cations of organic sulfides and disulfides formed by radiolysis: an elecron spin resonance study J. Chem. Soc., Perkin Trans. 2 1984 1681-1688.
27. H. Hirano S. Yakabe J. H. Clark T. Morimoto Synthesis of sulfoxides by the oxidation of sulfides with sodium chlorite catalysed by manganese(III) acetylacetonate in acetone in the presence of alumina J. Chem. Soc., Perkin Trans. 1 1996 2693-2698.
28. D. Barbas S. Spyroudis A. Varvoulis Oxidation of organic sulfides with [bis(trifluoroacetoxy)iodo]benzene J. Chem. Res. (M) 1985 2201-2214.
29. A. Greer F. Jensen E. L. Clennan Ring strain effects on the interconversion of intermediates in the reaction of organic sulfides with singlet oxygen J. Org. Chem. 1996 61 4107-4110.
30. E. Baciocchi T. Del Giacco F. Elisei M. F. 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 tetrafluoborate and 9,10-dicyanoanthracene. The probable involvement of a thiadioxirane intermediate in electron transfer photooxygenations J. Am. Chem. Soc. 2004 125 16444-16454.
31. E. A. Fehnel M. Carmack The ultraviolet absorption spectra of organic sulfur compounds. I Compounds containing the sulfide function J. Am. Chem. Soc. 1949 71 84-93.