Abstract
The photooxygenation of thiophenes, benzo[b]thiophenes and dibenzothiophenes is discussed, especially in view of the oxidative removal of these S-containing contaminants from fuels. Furthermore, the photochemistry of the intermediates and the products from these processes is detailed. Finally, an account is given of the electrooxidation of thiophenes and derivatives to the corresponding sulfoxides and sulfones as well as of the electrochemical behaviour of the intermediate thiophene S-oxides.
References
1.
Thiemann T.
,
Arima K.
, and
Mataka S.
, Rep. Inst. Adv. Mat. Kyushu Univ. , 2000 , 14 , 37 ; Chem. Abstr. , 2001, 134 , 173925.
2.
Zander M.
, Polycyclic Arom. Comp. , 1995 , 7 , 209 .
3.
Bundt J.
,
Herbst W.
, and
Steinhart H.
, J. High Res. Chromatogr. , 2005 , 15 , 682 .
4.
Palmentier J.-P.F.
,
Britten A.J.
,
Charbonneau G.M.
, and
Karasek F.W.
, J. Chromatogr. A , 1989 , 469 , 241 .
5.
Schmidt W.
,
Grimmer G.
,
Jacob J.
, and
Dettbarn G.
, Toxicol. Environm. Chem. , 1986 , 13 , 1 .
6.
Brunet S.
,
Mey D.
,
Perot G.
,
Bouchy C.
, and
Diehl F.
, Appl. Catal. A , 2005 , 278 , 143 .
7.
Campbell I.M.
, CHEMTECH , 1993 , 43 , 43 .
8.
Shiraishi Y.
,
Tachibana K.
,
Hirai T.
, and
Komasawa I.
, Ind. Eng. Chem. Res. , 2002 , 41 , 4362 .
9.
Otsuki S.
,
Nonaka T.
,
Takashima N.
,
Qian W.
,
Ishihara A.
,
Imai T.
, and
Kabe T.
, Energy Fuels , 2000 , 14 , 1232 .
10.
Wasserman H.H.
, and
Lipshutz B.H.
in Singlet oxygen , eds.
Wasserman H.H.
, and
Edwards R.W.
, Academic Press , New York , 1979 , p. 430 .
11.
Wasserman H.H.
, and
Strehlow W.
, Tetrahedron Lett. , 1970 , 11 , 795 .
12.
Iesce M.R.
,
Cermola F.
, and
Temussi F.
, Curr. Org. Chem. , 2005 , 9 , 109 .
13.
Ando W.
, and
Tarata in T.
Singlet oxygen , ed.
Frimer A.A.
, CRC Press , Boca Raton, Florida , 1985 , vol. 3 , p. 95 .
14.
Gollnick K.
, and
Griesbeck A.
, Tetrahedron Lett. , 1984 , 25 , 4291 .
15.
Chen C.-W.
, and
Ho C.-T.
, J. Agric. Food Chem. , 1996 , 44 , 2078 .
16.
Skold C.N.
, and
Schlessinger R.N.
, Tetrahedron Lett. , 1970 , 11 , 791 .
17.
Adam W.
, and
Eggelte H.J.
, Angew. Chem. Int. Ed. Engl. , 1978 , 17 , 765 .
18.
Matturro M.G.
, and
Reynolds R.P.
, Tetrahedron Lett. , 1987 , 28 , 4981 .
19.
Matturro M.G.
,
Reynolds R.P.
,
Kastrup R.V.
, and
Pictroski F.
, J. Am. Chem. Soc. , 1986 , 108 , 2775 .
20.
Adam W.
, and
Weinkötz S.
, J. Chem. Soc., Chem. Commun. , 1996 , 177 .
21.
Adam W.
,
Fröhling B.
,
Peters K.
, and
Weinkötz S.
, J. Am. Chem. Soc. , 1998 , 120 , 8914 .
22.
Adam W.
, and
Weinkötz S.
, Tetrahedron Lett. , 1995 , 36 , 7431 .
23.
Li F.
,
Zhao D.-S.
,
Li H.-X.
, and
Liu R.-H.
, Ann. Acad. Sci. N. Y. , 2008 , 1140 , 383 .
24.
Ibrahim A.
,
Xian S.B.
, and
Wei Z.
, Petrol. Sci. Technol. , 2003 , 21 , 1555 .
25.
Na P.
,
Zhao B.
,
Gu L.
, and
Na J.
, J. Phys. Chem. Solids , 2009 , 70 , 1465 .
26.
Jacquot F.
,
Guiliano M.
,
Doumenq F.
,
Munoz D.
, and
Mille G.
, Chemosphere , 1996 , 33 , 671 .
27.
Mill T.
,
Mabey W.R.
,
Lan B.Y.
, and
Baraze A.
, Chemosphere , 1981 , 10 , 1281 .
28.
Payne J.R.
, and
Phillips C.R.
, Environ. Sci. Technol. , 1985 , 19 , 569 .
29.
Berthou F.
, and
Vignier V.
, Int. J. Environ. Chem. , 1986 , 27 , 81 .
30.
Zhang J.
,
Zhao D.
,
Wang J.
, and
Yang L.
, J. Mat. Sci. , 2009 , 44 , 3112 .
31.
Zhao D.
,
Zhang J.
,
Wang J.
,
Liang W.
, and
Li H.
, Petroleum Sci. Technol. , 2009 , 27 , 1 .
32.
Shiraishi Y.
,
Hirai T.
, and
Komasawa I.
, Ind. Chem. Eng. Sci. , 1998 , 37 , 203 .
33.
Jenks W.S.
,
Lee W.
, and
Shutters D.
, J. Phys. Chem. , 1994 , 98 , 2282 .
34.
Jenks W.S.
,
Taylor L.M.
,
Guo Y.
, and
Wan Z.
, Tetrahedron Lett. , 1994 , 35 , 7155 .
35.
Shiraishi Y.
,
Hirai T.
, and
Komasawa I.
, Ind. Eng. Chem. Res. , 1999 , 38 , 3300 .
36.
Khudayer A.F.
, Diss. Abstr. Int., B , 1991 , 51 , 3303 .
37.
Andersson J.T.
, and
Bobinger S.
, Chemosphere , 1992 , 24 , 383 .
38.
Shiraishi Y.
,
Taki Y.
,
Hirai T.
, and
Komasawa I.
, Ind. Eng. Chem. Res. , 1999 , 38 , 3310 .
39.
Shiraishi Y.
,
Taki Y.
,
Hirai T.
, and
Komasawa I.
, J. Chem. Soc., Chem. Commun. , 1998 , 2601 .
40.
Yazu K.
,
Yamamoto Y.
,
Miki K.
, and
Ukegawa K.
, J. Oleo. Sci. , 2001 , 50 , 521 .
41.
Gondal M.A.
,
Masoudi H.M.
, and
Pola J.
, Chemosphere , 2008 , 71 , 1765 .
42.
Abdel-Wahab A.-M.A.
, and
Gaber A.E.-A.M.
, J. Photochem. Photobiol. , 1998 , 114 , 213 .
43.
Gurria G.M.
, and
Posner G.H.
, J. Org. Chem. , 1973 , 38 , 2419 .
44.
Shelton J.R.
, and
Davies K.E.
, Int. J. Sulfur Chem. , 1973 , 8 , 217 .
45.
Thiemann T.
,
Kumazoe K.
,
Arima K.
, and
Mataka S.
, Rep. Inst. Adv. Mat. Kyushu Univ. , 2001 , 15 (1 ), 63 ; Chem. Abstr. , 2002, 136 , 19802.
46.
Kumazoe K.
,
Arima K.
,
Mataka S.
,
Walton D.J.
, and
Thiemann T.
, J. Chem. Res. , 2003 , (S) 60 ; J. Chem. Res. , (M) 248.
47.
Wan Z.
, and
Jenks W.S.
, J. Am. Chem. Soc. , 1995 , 117 , 2667 .
48.
Gregory D.D.
,
Wan Z.
, and
Jenks W.S.
, J. Am Chem. Soc. , 1997 , 119 , 94 .
49.
Lucien E.
, and
Greer A.
, J. Org. Chem. , 2001 , 66 , 4576 .
50.
Thomas K.B.
, and
Greer A.
, J. Org. Chem. , 2003 , 68 , 1886 .
51.
Korang J.
,
Grither W.R.
, and
McCulla R.D.
, J. Am. Chem. Soc. , 2010 , 132 , 4466 .
52.
Rockafellow E.M.
,
McCulla R.D.
, and
Jenks W.S.
, J. Photochem. Photobiol. A , 2008 , 198 , 45 .
53.
de Lucas N.C.
,
Albuquerque A.C.C.
,
Santos A.C.A.S.
,
Garden S.J.
, and
Nicodem D.E.
, J. Photochem. Photobiol. A , 2007 , 188 , 293 .
54.
Wang C.
, and
Weiss R.G.
, Macromolecules , 1999 , 32 , 7032 .
55.
Geneste P.
,
Grimaud J.
,
Olive J.L.
, and
Ung S.N.
, Bull. Soc. Chim. Fr. , 1977 , 271 .
56.
El Faghi El Amoudi M.S.
,
Geneste P.
, and
Olive J.L.
, Tetrahedron Lett. , 1978 , 19 , 999 .
57.
El Faghi El Amoudi M.S.
,
Geneste P.
, and
Olive J.L.
, J. Org. Chem. , 1981 , 46 , 4258 .
58.
Davies W.
, and
James F.C.
, J. Chem. Soc. , 1955 , 314 .
59.
Mustafa A.
, and
Zayed S.M.A.
, J. Am. Chem. Soc. , 1976 , 98 , 3254 .
60.
Hopkinson M.J.
,
Schloman W.W.
Jr.
,
Plummer B.F.
,
Wenkert E.
, and
Raju M.
, J. Am. Chem. Soc. , 1979 , 101 , 2157 .
61.
Davies W.
,
Ennis B.C.
,
Mahavera C.
, and
Porter Q.N.
, Aust. J. Chem. , 1977 , 30 , 173 .
62.
Haines W.E.
,
Helm R.V.
,
Cook G.L.
, and
Ball J.S.
, J. Phys. Chem. , 1956 , 60 , 549 .
63.
Thiemann C.
,
Thiemann T.
,
Li Y.Q.
,
Sawada T.
,
Nagano Y.
, and
Tashiro M.
, Bull. Chem. Soc. Jpn. , 1994 , 67 , 1886 .
64.
Arima K.
,
Ohira D.
,
Watanabe M.
,
Miura A.
,
Mataka S.
,
Thiemann T.
,
Iniesta Valcarcel J.
, and
Walton D.J.
, Photochem. Photobiol. Sci. , 2005 , 4 , 808 .
65.
Nakayama J.
,
Hiraiwa S.
, and
Fujihara T.
, J. Sulfur Chem. , 2008 , 29 , 243 .
66.
Heying M.J.
,
Nag M.
, and
Jenks W.S.
, J. Phys. Org. Chem. , 2008 , 21 , 915 .
67.
Bongini A.
,
Barbarella G.
,
Zambianchi M.
,
Arbizzani C.
, and
Mastra-gostino M.
, Chem. Commun. , 2000 , 439 .
68.
Thiemann T.
,
Ohira D.
,
Arima K.
,
Sawada T.
,
Mataka S.
,
Marken F.
,
Compton R.G.
,
Bull S.D.
, and
Davies S.G.
, J. Phys. Org. Chem. , 2000 , 13 , 648 .
69.
Iniesta J.
,
Alcock H.
,
Walton D.J.
,
Watanabe M.
,
Mataka S.
, and
Thiemann T.
, Electrochim. Acta , 2006 , 51 , 5682 .
70.
Iniesta J.
,
Walton D.J.
,
Fujii H.
,
Thiemann T.
,
Tanaka Y.
,
Mataka S.
,
Mason T.J.
, and
Lorimer J.P.
, Ultrasonics Sonochem. , 2004 , 11 , 227 .
71.
Kim I.K.
, and
Jung O.J.
, Bull. Korean Chem. Soc. , 2002 , 23 , 990 .
72.
Wu Z.
, and
Ondruska B.
, Ultrasonics Sonochem. , 2006 , 13 , 86 .
73.
SRC PhysProp Database, http://www.syrres.com/esc/physdemo.htm.
74.
Zanardi C.
,
Scanu R.
,
Pigani L.
,
Pilo M.I.
,
Sanna G.
,
Seeber R.
,
Spano N.
,
Terzi F.
, and
Zucca A.
, Electrochim. Acta , 2006 , 51 , 4859 .
75.
An H.
, and
Seki M.
, Makromol. Chem., Rapid Commun. , 1987 , 8 , 325 .
76.
Cariou M.
,
Douadi T.
, and
Simonet J.
, New J. Chem. , 1995 , 19 , 65 .
77.
Barsch U.
, and
Beck F.
, Electrochim. Acta , 1996 , 41 , 1761 .
78.
Houghton D.S.
, and
Humffray A.A.
, Electrochim. Acta , 1972 , 17 , 2145 .
79.
Izumi I.
, and
Yamamoto I.
, Denki Kagaku oyobi Kogyo Butsuri Kagaku , 1983 , 51 , 333 ; Chem. Abstr. , 1983, 99 , 52862.
80.
Wang W.
,
Wang S.
,
Liu H.
, and
Wang Z.
, Fuel , 2007 , 86 , 2747 .
81.
Wang W.
,
Wang S.
,
Wang Y.
,
Liu H.
, and
Wang Z.
, Fuel Process Technol. , 2007 , 88 , 1002 .
82.
Suh M.C.
,
Jiang B.T.
, and
Tilley T.D.
, Angew. Chem. Int. Ed. Engl. , 2000 , 39 , 2870 .
