Browse > Article
http://dx.doi.org/10.5012/bkcs.2006.27.1.106

Photoinduced Electron Transfer Reactions of Aryl Benzyl Sulfides Promoted by 2,4,6-Triphenylpyrilium Tetrafluoroborate (TP+BF4-)  

Memarian, Hamid Reza (Faculty of Science, Department of Chemistry, University of Isfahan)
Ira, Mohammadpoor Baltork (Faculty of Science, Department of Chemistry, University of Isfahan)
Bahrami, Kiumars (Faculty of Science, Department of Chemistry, University of Isfahan)
Publication Information
Bulletin of the Korean Chemical Society / v.27, no.1, 2006 , pp. 106-110 More about this Journal
Abstract
Photocatalytic electron transfer reactions of aryl benzyl sulfides using 2,4,6 triphenylpyrilium tetrafluoroborate ($TP^+BF_4^-$) resulted in the oxidation of these sulfides to the corresponding sulfoxides and also in most cases in the C-S bond cleavage of them along with formation of aromatic aldehydes. In these reactions, the formation of sulfide radical cation has been proposed, which undergoes either oxidation to the corresponding sulfoxide or C-S bond cleavage to the formation of aromatic aldehydes. The further oxidation of sulfoxides to sulfones has not been observed. The influence of substrate structures on the reaction pathways as well as the role of $O_2$ in this respect is discussed.
Keywords
Electron transfer; Aryl benzyl sulfides; Sulfoxides; Photocleavage; Photochemistry;
Citations & Related Records

Times Cited By Web Of Science : 3  (Related Records In Web of Science)
Times Cited By SCOPUS : 4
연도 인용수 순위
1 Oae, S.; Takata, T.; Kim, Y. H. Tetrahedron 1981, 37, 37   DOI   ScienceOn
2 Miranda, M. A.; Garcia, H. Chem. Rev. 1994, 94, 1063   DOI   ScienceOn
3 Sinnreich, D.; Lind, H.; Batzer, H. Tetrahedron Lett. 1976, 3541
4 Tezuka, T.; Miyazaki, H.; Suzuki, H. Tetrahedron Lett. 1978, 1959
5 Akasaka, T.; Yabe, A.; Ando, W. J. Am. Chem. Soc. 1987, 109, 8085   DOI
6 Vialaton, D.; Richard, C. J. Photochem. Photobiol. A: Chem. 2000, 136, 169   DOI   ScienceOn
7 Bhalerao, U. T.; Sridhar, M. Tetrahedron Lett. 1994, 35, 1413   DOI   ScienceOn
8 Bonesi, S. M.; Albini, A. J. Org. Chem. 2000, 65, 4532   DOI   ScienceOn
9 Madhavan, D.; Pitchumani, K. Tetrahedron 2001, 57, 8391   DOI   ScienceOn
10 Bonesi, S. M.; Fagoni, M.; Monti, S.; Albini, A. Photochem. Photobiol. Sci. 2004, 3, 489   DOI   ScienceOn
11 Mattes, S. L.; Farid, S. J. Am. Chem. Soc. 1986, 108, 7356   DOI
12 Ericksen, J.; Foote, C. S.; Parker, T. L. J. Am. Chem. Soc. 1977, 99, 6455   DOI
13 Galindo, F.; Miranda, M. A. J. Photochem. Photobiol. A: Chem. 1998, 113, 155   DOI   ScienceOn
14 Wong, P. C.; Arnold, D. R. Tetrahedron Lett. 1979, 23, 2101
15 Shima, K.; Sazaki, A.; Nakabayashi, K.; Yasuda, M. Bull. Chem. Soc. Jpn. 1992, 65, 1472   DOI   ScienceOn
16 Memarian, H. R.; Hesami, A.; Nikpour, F.; Döpp, D. Indian J. Chem. 2001, 40B, 662
17 Memarian, H. R.; Nikpour, F. Chem. Mon. 2002, 133, 1045   DOI   ScienceOn
18 Memarian, H. R.; Nikpour, F. Molecules 2002, 7, 63   DOI
19 Memarian, H. R.; Nikpour, F. J. Chin. Chem. Soc. 2002, 49, 401
20 Corey, E. J.; Ouanennes, C. Tetrahedron Lett. 1976, 4263
21 Toutchkine, A.; Clennan, E. L. J. Am. Chem. Soc. 2000, 122, 1834   DOI   ScienceOn
22 Akaba, R.; Aihars, S.; Sakuragi, H.; Tokumaru, K. J. Chem. Soc. Chem. Commun. 1987, 1262
23 Akaba, R.; Sakuragi, H.; Tokumaru, K. J. Chem. Soc. Perkin Trans. 2 1991, 291
24 Purdie, J. W. Can. J. Chem. 1971, 49, 725   DOI
25 Ali, M. H.; Leach, D. R.; Schmitz, C. E. Synth. Commun. 1998, 28, 2969   DOI   ScienceOn
26 Clark, N. G.; Cranham, J. E.; Greenwood, D.; Marshall, J. R.; Stevenson, H. A. J. Sci. Food Agric. 1957, 8, 566   DOI
27 Choudary, B. M.; Bharathi, B.; Venkat Reddy, Ch.; Lakshmi Kantam, M. J. Chem. Soc., Perkin Trans. 1 2002, 2069
28 Davidson, R. S.; Goodin, J. W.; Pratt, J. E. Tetrahedron Lett. 1982, 23, 2225   DOI   ScienceOn
29 Davidson, R. S.; Partt, J. E. Tetrahedron Lett. 1983, 24, 5903   DOI   ScienceOn
30 Baciocchi, E.; Giacco, T. D.; Elisei, F.; Gerini, M. F.; Guerra, M.; Lapi, A.; Liberali, P. J. Am. Chem. Soc. 2003, 125, 16444   DOI   ScienceOn
31 Ando, W.; Nagashima, T.; Saito, K.; Kohmoto, S. J. Chem. Soc. Chem. Commun. 1979, 154
32 Jensen, F.; Greer, A.; Clennan, E. L. J. Am. Chem. Soc. 1998, 120, 4439   DOI   ScienceOn
33 Drabowicz, J.; Midura, W.; Mikolajczyk, M. Synthesis 1979, 39
34 Kamata, M.; Sato, M.; Hasegawa, E. Tetrahedron Lett. 1992, 33, 5085   DOI   ScienceOn
35 Watanabe, Y.; Numata, T.; Oae, S. Synthesis 1981, 204
36 Zhang, W.; Jia, X.; Yang, L.; Liu, Z.-L. Tetrahedron Lett. 2002, 43, 9433   DOI   ScienceOn
37 Brookes, R. F.; Clark, N. G.; Cranham, J. E.; Greenwood, D.; Marshall, J. R.; Stevenson, H. A. J. Sci. Food Agric. 1958, 9, 111   DOI
38 Lacombe, S.; Cardy, H.; Simon, M.; Khoukh, A.; Soumillion, J. Ph.; Ayadim, M. Photochem. Photobiol. Sci. 2002, 1, 347   DOI   ScienceOn
39 Baciocchi, E.; Crescenzi, C.; Lanzalunga, O. Tetrahedron 1997, 53, 4469   DOI   ScienceOn
40 Baciocchi, E.; Del Giacco, T.; Ferrero, M. I.; Rol, C.; Sebastiani, G. V. J. Org. Chem. 1997, 62, 4015   DOI   ScienceOn
41 Gu, C.-L.; Foote, C. S.; Kacher, M. L. J. Am. Chem. Soc. 1981, 103, 5949   DOI
42 Vogel's Textbook of Practical Organic Chemistry, 5th ed.; Longmann Scientific & Technical: Essex, 1989; p 789
43 Hafner, K.; Kaiser, H. Organic Synthesis; Wiley: New York, 1973; Coll. Vol. 5, p 1088
44 Shiraishi, Y.; Taki, Y.; Hirai, T.; Komasawa, I. Chem. Commun. 1998, 2601
45 Soggiu, N.; Cardy, H.; Habib Jiwan, J. L.; Leray, I.; Soumillion, J. Ph.; Lacombe, S. J. Photochem. Photobiol. A: Chem. 1999, 124, 1   DOI   ScienceOn
46 Foote, C. S.; Peters, J. W. J. Am. Chem. Soc. 1971, 93, 3795   DOI
47 Sawaki, Y.; Ogata, Y. J. Am. Chem. Soc. 1981, 103, 5947   DOI