Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2004(6): 971-974
DOI: 10.1055/s-2004-820041
DOI: 10.1055/s-2004-820041
LETTER
© Georg Thieme Verlag Stuttgart · New York
[60]Fullerene Supported on Silica and γ-Alumina Sensitized Photooxidation of Olefins: Chemical Evidence for Singlet Oxygen and Electron Transfer Mechanism
Further Information
Received
31 January 2004
Publication Date:
25 March 2004 (online)
Publication History
Publication Date:
25 March 2004 (online)
Abstract
Fullerene C60 supported on silica and γ-alumina (2% w/w C60/SiO2 and C60/Al2O3) sensitizes the photooxidation of alkenes via singlet oxygen and/or electron transfer mechanism, depending on the solvent and the substrate.
Key words
heterogeneous photooxidations - fullerene C60 - alkenes - singlet oxygen - electron transfer
-
1a
Arbogast JW.Darmanyan AP.Foote CS.Rubin Y.Diederich FN.Alvarez MM.Anz SJ.Whetten RL. J. Phys. Chem. 1991, 95: 11 -
1b
Arbogast JW.Foote CS. J. Am. Chem. Soc. 1991, 113: 8886 -
2a
Wasielewski MR.O’Neil MP.Lykke KR.Pellin MJ.Gruen DM. J. Am. Chem. Soc. 1991, 113: 2774 -
2b
Fraelich MR.Weisman RB. J. Phys. Chem. 1993, 97: 11145 - For singlet oxygen reviews see:
-
3a
Stratakis M.Orfanopoulos M. Tetrahedron 2000, 56: 1595 -
3b
Clennan EL. Tetrahedron 2000, 56: 9151 -
3c
Jefford CW. Chem. Soc. Rev. 1993, 22: 59 -
3d
Foote CS.Cleenan EL. Active Oxygen in ChemistryFoote CS.Valentine JS.Greenberg A.Liebman JF. Chapman and Hall; London: 1995. p.105-140 -
4a
Ito O.Sasaki Y.Yoshikawa Y.Watanabe A. J. Phys. Chem. 1995, 99: 9838 -
4b
Sasaki Y.Yoshikawa Y.Watanabe A.Ito O. J. Chem. Soc., Faraday Trans. 1995, 91: 2287 -
4c
Fukuzumi S.Suenobu T.Patz M.Hirasaka T.Itoh S.Fujitsuka M.Ito O. J. Am. Chem. Soc. 1998, 120: 8060 -
5a
Zhang X.Romero A.Foote CS. J. Am. Chem. Soc. 1993, 115: 11024 -
5b
An Y.-Z.Viado AL.Arce M.-J.Rubin Y. J. Org. Chem. 1995, 60: 8330 -
5c
Chronakis N.Vougioukalakis GC.Orfanopoulos M. Org. Lett. 2002, 4: 945 -
6a
Orfanopoulos M.Kambourakis S. Tetrahedron Lett. 1994, 35: 1945 -
6b
Tokuyama H.Nakamura E. J. Org. Chem. 1994, 59: 1135 -
6c
Orfanopoulos M.Kambourakis S. Tetrahedron Lett. 1995, 36: 435 -
7a
Jensen AW.Daniels C. J. Org. Chem. 2003, 68: 207 -
7b
Nie B.Hasan K.Greaves MD.Rotello VM. Tetrahedron Lett. 1995, 36: 3617 -
7c
Guhr KI.Greaves MD.Rotello VM. J. Am. Chem. Soc. 1994, 116: 5997 - 8 The photooxidation of benzene and cyclohexene by the use of C60 and C70, grafted on mesoporous FSM-16 as photosensitizers, was recenlty reported. See:
Fukuoka A.Fujishima K.Chiba M.Yamagishi A.Inagaki S.Fukushima Y.Ichikawa M. Catal. Lett. 2000, 68: 241 - 9
Vakros J.Panagiotou G.Kordulis C.Lycourghiotis A.Vougioukalakis GC.Angelis Y.Orfanopoulos M. Catal. Lett. 2003, 89: 269 - For experimental details of the above techniques see:
-
10a
Georgiadu I.Papadopoulou Ch.Matralis HK.Voyiatzis GA.Lycourghiotis A.Kordulis Ch. J. Phys. Chem. B 1998, 102: 8459 -
10b
Vakros J.Kordulis Ch.Lycourghiotis A. Langmuir 2002, 18: 417 -
11a
Ramamurthy V.Lakshminarasimhan P.Grey PC.Johnston LJ. Chem. Commun. 1998, 2411 -
11b
Stratakis M.Nencka R.Rabalakos C.Adam W.Krebs O. J. Org. Chem. 2002, 67: 8758 -
12a
Ogilby PR.Foote CS. J. Am. Chem. Soc. 1983, 105: 3423 -
12b
Hurst JR.Schuster GB. J. Am. Chem. Soc. 1983, 105: 5756 - 13
Eriksen J.Foote CS. J. Am. Chem. Soc. 1980, 102: 6083 - 14
Stephenson LM.Grdina MJ.Orfanopoulos M. Acc. Chem. Res. 1980, 13: 419 - 15
An Y.-Z.Chen CB.Anderson JL.Sigman DS.Foote CS.Rubin Y. Tetrahedron 1996, 52: 5179 - 16
Bartlett PD.Landis ME. J. Am. Chem. Soc. 1977, 99: 3033 -
17a
Gollnick K.Schnatterer A. Tetrahedron Lett. 1984, 25: 185 -
17b
Gollnick K.Schnatterer A. Tetrahedron Lett. 1984, 25: 2735