SPECIAL TOPIC
Sustainable Oxidations in Water
1977
Oxidation of Olefins
(22) Hill, C. L.; Bouchard, D. A. J. Am. Chem. Soc. 1985, 107,
5148.
(23) Misono, M.; Einaga, H. Bull. Chem. Soc. Jpn. 1997, 70,
1551.
(24) Bonchio, M.; Carraro, M.; Conte, V.; Scorrano, G. Eur. J.
Org. Chem. 2005, 4897.
(25) Bonchio, M.; Carraro, M.; Gardan, M.; Scorrano, G.; Drioli,
E.; Fontananova, E. Adv. Synth. Catal. 2003, 345, 1119.
(26) Bonchio, M.; Carraro, M.; Gardan, M.; Scorrano, G.; Drioli,
E.; Fontananova, E. Top. Catal. 2006, 40, 133.
(27) (a) Maldotti, A.; Molinari, A.; Bigi, F. J. Catal. 2008, 253,
312. (b) Molinari, A.; Amadelli, R.; Mazzacani, A.; Sartori,
G.; Maldotti, A. Langmuir 2002, 18, 5400. (c) Maldotti, A.;
Molinari, A.; Varani, G.; Lenarda, M.; Storaro, L.; Bigi, F.;
Maggi, R.; Mazzacani, A.; Sartori, G. J. Catal. 2002, 209,
210.
cis-Cyclooctene or cyclohexene (0.51 mmol) were suspended in
deionized H O (5 mL) containing NaIO (1.95 mmol) and
2
4
Li [Ru(DMSO)PW O ] (5 mmol); the suspension was vigorously
5
11 39
stirred at 50 °C for 4 h; unreacted alkene and oxidation products
1
were then extracted with Et O (5 × 5 mL) analyzed by GC-FID, H
2
and 13C NMR.
Asymmetric Oxidation of Thioanisole
PhSMe was suspended in aq 0.05 M HEPES buffer soln (pH 7, 5
mL) with the appropriate amounts of Na MoO , bCD-derivative,
2
4
and 35% H O in H O, and the mixture was placed in a jacketed
2
2
2
glass vial with temperature control (T = 20 °C). After 2 h the mix-
ture was extracted with CH Cl (5 mL) and the organic phase was
2
2
washed with sat. Na S O soln and subsequently with H O, dried
2
2
5
2
(
anhyd MgSO ), and concentrated under vacuum.
4
(28) Tanielian, C.; Duffy, K.; Jones, A. J. Phys. Chem. B 1997,
1
01, 4276.
Acknowledgment
(
(
29) Vankelecom, I. F. J. Chem. Rev. 2002, 102, 3779.
30) Mulder, M. Basic Principles of Membrane Technology, Vol.
III; Kluwer Academic Publishers: Dortrecht, 1996, 71.
31) Vankelecom, I. F. J.; Jacobs, P. A. Catal. Today 2000, 56,
Financial support from CNR, MIUR (FIRBCAMERE-
RBNE03JCR5, PRIN contract No. 2006034372), and the ESF
COST D40 action is gratefully acknowledged.
(
(
(
147.
32) Carraro, M.; Gardan, G.; Drioli, E.; Fontananova, E.;
Bonchio, M. Chem. Commun. 2006, 4533.
33) (a) Singlet Oxygen; Wasserman, H.; Murray, R. W., Eds.;
Academic Press: New York, 1979. (b) Singlet Oxygen;
Frimer, A. A., Ed.; CRC Press: Boca Raton FL, 1985.
(34) Clennan, E. L. Tetrahedron 2000, 56, 9151.
(35) Griesbeck, A. G.; Bartoschek, A. Chem. Commun. 2002,
1594.
(36) Legrini, O.; Oliveros, E.; Braun, A. M. Chem. Rev. 1993, 93,
671.
References
(
(
(
1) Szaciłowski, K.; Macyk, W.; Drzewiecka-Matuszek, A.;
Brindell, M.; Stochel, G. Chem. Rev. 2005, 105, 2647.
2) Maldotti, A.; Molinari, A.; Amadelli, R. Chem. Rev. 2002,
102, 3811.
3) Active Oxygen in Chemistry; Foote, C. S.; Valentine, J. S.;
Greenberg, A.; Liebman, J. F., Eds.; Chapman & Hall:
London, 1995.
(
4) Pope, M. T. Heteropoly and Isopoly Oxometalates; Springer
Verlag: New York, 1983.
(37) Gerdes, R.; Wohrle, D.; Spiller, W.; Schneider, G.;
Schnurpfeil, G.; Schulz-Ekloff, G. J. Photochem. Photobiol.
A: Chem. 1997, 111, 65.
(38) Li, C.; Hoffman, M. Z. J. Phys. Chem. A 2000, 104, 5998.
(39) (a) Kalyanasundaram, K. Photochemistry of Polypyridine
and Porphyrin Complexes; Academic Press: London, 1992.
(b) White, W. I. In The Porphyrins, Vol. I; Dolphin, D., Ed.;
Academic Press: London, 1978, 303.
(40) (a) Irngartinger, H.; Weber, A.; Escher, T. Eur. J. Org.
Chem. 2000, 1647. (b) Tajima, Y.; Arai, H.; Tezuka, Y.;
Ishii, T.; Takeuchi, K. Fullerene Sci. Technol. 1997, 5,
1531. (c) Poon, T. H. W.; Pringle, K.; Foote, C. S. J. Am.
Chem. Soc. 1995, 117, 7611. (d) Orfanopoulos, M.;
Kambourakis, S. Tetrahedron Lett. 1994, 35, 1945.
(41) Bonchio, M.; Maggini, M.; Menna, E.; Scorrano, G.;
Garlaschelli, L.; Giacometti, A.; Paolucci, F.; Gasparrini, F.;
Misiti, D.; Villani, C. In Recent Advances in the Chemistry
and Physics of Fullerenes and Related Materials, Vol. 99-
12; Kadish, K. M.; Guldi, D. M.; Kamat, P. V., Eds.; The
Electrochemical Society, Inc.: Pennington NY, 1999, 220.
(42) (a) Carofiglio, T.; Fornasier, R.; Lucchini, V.; Rosso, C.;
Tonellato, U. Tetrahedron Lett. 1996, 37, 8019.
(b) Carofiglio, T.; Fornasier, R.; Gennari, G.; Lucchini, V.;
Limonato, L.; Tonellato, U. Tetrahedron Lett. 1997, 38,
7919.
(
(
5) Special issue: Polyoxometalates Chem. Rev. 1998, 98, 1.
6) Pope, M. T.; Müller, A. Polyoxometalate Chemistry. From
Topology Via Self-assembly to Applications; Kluwer
Academic Publishers: Dortrecht, 2002.
(
7) Hill, C. L.; Prosser-McCartha, C. M. In Photosensitization
and Photocatalysis Using Inorganic and Organometallic
Compounds; Kalyanasundaram, K.; Grätzel, M., Eds.;
Kluwer Academic Publishers: Dortrecht, 1993, 307.
8) (a) Hiskia, A.; Mylonas, A.; Papaconstantinou, E. Chem.
Soc. Rev. 2001, 30, 62. (b) Papaconstantinou, E. Chem. Soc.
Rev. 1989, 18, 1.
(
(
9) Fox, M. A.; Cardona, R.; Gailard, E. J. Am. Chem. Soc.
1
987, 109, 6347.
(
(
10) Hiskia, A.; Papaconstantinou, E. Polyhedron 1988, 7, 477.
11) Duncan, D. C.; Netzel, T. L.; Hill, C. L. Inorg. Chem. 1995,
34, 4640.
(
(
(
12) Texier, I.; Delaire, J. A.; Giannotti, C. Phys. Chem. Chem.
Phys. 2000, 2, 1205.
13) Tanielian, C.; Seghrouchni, R.; Schweitzer, C. J. Phys.
Chem. A 2003, 107, 1102; and references therein.
14) Nosaka, Y.; Takei, T.; Fujii, N. J. Photochem. Photobiol., A
1
995, 173.
(
(
15) Ozer, R. R.; Ferry, J. L. J. Phys. Chem. B 2000, 104, 9444.
16) Mylonas, A.; Hiskia, A.; Androulaki, E.; Dimotikali, D.;
Papaconstantinou, E. Phys. Chem. Chem. Phys. 1999, 1, 437.
17) Hill, C. L. Synlett 1995, 127.
18) Hill, C. L.; Zheng, Z. Chem. Commun. 1998, 2467.
19) Chambers, R. C.; Hill, C. L. Inorg. Chem. 1989, 28, 2509.
20) Hiskia, H.; Papaconstantinou, E. Inorg. Chem. 1992, 31,
(43) Bonchio, M.; Carofiglio, T.; Carraro, M.; Fornasier, R.;
Tonellato, U. Org. Lett. 2002, 4, 4635.
(44) Kano, K.; Nishiyabu, R.; Asada, T.; Kuroda, Y. J. Am.
Chem. Soc. 2002, 124, 9937.
(45) Tanelian, C.; Wolff, C.; Esch, M. J. Phys. Chem. 1996, 100,
6555.
(46) Breslow, R.; Yang, J.; Yan, J. M. Tetrahedron 2002, 58, 653.
(47) Baugh, S. D. P.; Yang, Z.; Leung, D. K.; Wilson, D. M.;
Breslow, R. J. Am. Chem. Soc. 2001, 123, 12488.
(
(
(
(
1
63.
21) Akid, R.; Darwent, J. R. J. Chem. Soc., Dalton Trans. 1985,
95.
(
3
Synthesis 2008, No. 12, 1971–1978 © Thieme Stuttgart · New York