J.-Y. Piquemal, L. Salles, G. Chottard, P. Herson, C. Ahcine, J.-M. Brégeault
FULL PAPER
[22]
J.-M. Brégeault, C. Aubry, G. Chottard, N. Platzer, F. Chau-
veau, C. Huet, H. Ledon, Stud. Surf. Sci. Catal. 1991, 66, 521–
529.
C. Aubry, G. Chottard, N. Platzer, J.-M. Brégeault, F. Chau-
veau, C. Huet, H. Ledon, Inorg. Chem. 1991, 30, 4409–4416.
J. Server-Carrio, J. Bas-Serra, M. E. Gonzales-Nunez, A. Gar-
cia-Gastaldi, G. B. Jameson, L. C. W. Baker, R. Acerete, J. Am.
Chem. Soc. 1999, 121, 977–984.
L. Salles, R. Thouvenot, J.-M. Brégeault, Dalton Trans. 2004,
904–907.
T. Yamase, T. Ozeki, S. Motomura, Bull. Chem. Soc. Jpn. 1992,
65, 1453–1459.
T. Yamase, E. Ishikawa, Y. Asai, S. Kanai, J. Mol. Catal. A:
Chem. 1996, 114, 237–245.
O. A. Kholdeeva, T. A. Trubitsina, M. N. Timofeeva, G. M.
Maksimov, R. I. Maksimovskaya, V. A. Rogov, J. Mol. Catal.
A: Chem. 2005, 232, 173–178.
J.-M. Brégeault, C. Lepetit, F. Ziani-Derdar, O. Mohammedi,
L. Salles, A. Deloffre, Stud. Surf. Sci. Catal. 1997, 110, 545–
556.
J.-M. Brégeault, R. Thouvenot, S. Zoughebi, L. Salles, A. At-
lamsani, E. Duprey, C. Aubry, F. Robert, G. Chottard, Stud.
Surf. Sci. Catal. 1994, 82, 571–581.
techniques and deaerated solvents. (R)-(+)-Limonene (1.5 mmol)
was rapidly added to a thermostatted (20 °C) solution of the com-
plex (0.25 mmol for XW2 and 0.125 mmol for XW4 or XMo4,
active oxygen content, i.e. [O2]2–: 1 mmol) in dry CH2Cl2 (5 mL).
The solution was stirred under dinitrogen. GC analyses were per-
formed periodically with n-decane as internal standard. (R)-(+)-
Limonene oxide (mixture of cis and trans) was obtained and iso-
lated. It was identified by MS and by 1H and 13C NMR spec-
troscopy.[13]
[23]
[24]
[25]
[26]
[27]
[28]
Catalysis Tests: Our previous procedure[13,23] was followed.
“H2WO4” was treated with 15% H2O2 (4 mL, 19.6 mmol). After
15 min of stirring (necessary for the precursor to react completely
at 60 °C) and cooling at room temperature, Na2H[AsO4]·7H2O was
added (see Table 3). Q+Cl–, dissolved in the organic solvent, was
then added with the substrate (6.2 mmol). The two-phase mixture
was stirred vigorously (1200 rpm) for 6 h at 20 °C under dinitrogen.
The organic extract was analysed by GC and/or GC–MS and in
[29]
[30]
1
some cases by H NMR spectroscopy.
Acknowledgments
[31]
[32]
[33]
[34]
L. Salles, J.-M. Brégeault, R. Thouvenot, C. R. Acad. Sci., Ser.
IIc: Chim. 2000, 3, 183–187.
E. Duprey, J. Maquet, P. P. Man, J.-M. Manoli, M. Delamar,
J.-M. Brégeault, Appl. Catal., A 1995, 128, 89–96.
J.-Y. Piquemal, E. Briot, M. Vennat, J.-M. Brégeault, G. Chot-
tard, J.-M. Manoli, Chem. Commun. 1999, 1195–1196.
J.-Y. Piquemal, J.-M. Manoli, P. Beaunier, A. Ensuque, P.
Tougne, A.-P. Legrand, J.-M. Brégeault, Microporous Mesopo-
rous Mater. 1999, 29, 291–304.
E. Briot, J.-Y. Piquemal, M. Vennat, J.-M. Brégeault, G. Chot-
tard, J.-M. Manoli, J. Mater. Chem. 2000, 10, 953–958.
J.-M. Brégeault, J.-Y. Piquemal, E. Briot, E. Duprey, F. Lau-
nay, L. Salles, M. Vennat, A.-P. Legrand, Microporous Mesopo-
rous Mater. 2001, 44–45, 409–417.
We thank Dr. John Lomas for constructive discussions and for cor-
recting the manuscript, and Mme F. Sarrazin for preparing the text.
[1] C. L. Hill, C. M. Prosser-McCartha, Coord. Chem. Rev. 1995,
143, 407–455.
[2] T. Okuhara, N. Mizuno, M. Misono, Adv. Catal. 1996, 41, 113–
[35]
[36]
252.
[3] R. Neumann, Prog. Inorg. Chem. 1998, 47, 317–370.
[4] I. V. Kozhevnikov, Chem. Rev. 1998, 98, 171–198.
[5] C. Jost, G. Wahl, D. Kleinhenz, J. Sundermeyer in Peroxide
Chemistry (Ed.: W. Adam), Wiley-VCH Verlag GmbH,
Weinheim, 2000, pp. 341–364.
[6] J.-M. Brégeault, Dalton Trans. 2003, 3289–3302.
[7] N. Mizuno, K. Yamaguchi, K. Kamata, Coord. Chem. Rev.
2005, 249, 1944–1956.
[8] R. G. Beiles, Z. E. Rozmanova, O. B. Andreeva, Zh. Neorg.
Khim. 1969, 14, 2139–2142.
[9] L. Salles, C. Aubry, F. Robert, G. Chottard, R. Thouvenot, H.
Ledon, J.-M. Brégeault, New J. Chem. 1993, 17, 367–375.
[10] C. Venturello, R. d’Aloisio, J. C. J. Bart, M. Ricci, J. Mol. Ca-
tal. 1985, 32, 107–110.
[11] C. Venturello, R. d’Aloisio, J. C. J. Bart, M. Ricci, European
Patent Appl. 0146374, 1985.
[12] C. Venturello, M. Gambaro, J. Org. Chem. 1991, 56, 5924–
5931.
[13] L. Salles, C. Aubry, R. Thouvenot, F. Robert, C. Dorémieux-
Morin, G. Chottard, H. Ledon, Y. Jeannin, J.-M. Brégeault,
Inorg. Chem. 1994, 33, 871–878.
[14] J.-Y. Piquemal, L. Salles, C. Bois, F. Robert, J.-M. Brégeault,
C. R. Acad. Sci., Ser. IIb: Mec., Phys., Chim., Astron. 1994,
319, 1481–1487.
[37]
[38]
E. Briot, J.-Y. Piquemal, J.-M. Brégeault, New J. Chem. 2002,
26, 1443–1447.
J.-Y. Piquemal, E. Briot, G. Chottard, P. Tougne, J.-M. Manoli,
J.-M. Brégeault, Microporous Mesoporous Mater. 2003, 58,
279–289.
J.-Y. Piquemal, C. Bois, J.-M. Brégeault, Chem. Commun. 1997,
473–474.
J.-Y. Piquemal, S. Halut, J.-M. Brégeault, Angew. Chem. Int.
Ed. Engl. 1998, 37, 1146–1149.
L. J. Csanyi, K. Jacky, J. Catal. 1991, 127, 42–50.
A. C. Dengel, W. P. Griffith, B. C. Parkin, J. Chem. Soc., Dal-
ton Trans. 1993, 2683–2688.
L. Salles, J.-Y. Piquemal, R. Thouvenot, C. Minot, J.-M.
Brégeault, J. Mol. Catal. A: Chem. 1997, 117, 375–387.
O. W. Howarth, Dalton Trans. 2004, 476–481.
M. A. G. Aranda, J. P. Attfield, S. Bruque, M. Martinez-Lara,
Inorg. Chem. 1992, 31, 1045–1049.
M. I. Khan, Y. Chang, Q. Chen, H. Hope, S. Parking, D. P.
Goshorn, J. Zubieta, Angew. Chem. Int. Ed. Engl. 1992, 31,
1197–1200.
J.-M. Le Carpentier, A. Mitschler, R. Weiss, Acta Crystallogr.
Acta Crystallogr., Sect. B 1972, 28, 1278–1288.
W. P. Griffith, A. M. Z. Slawin, K. M. Thompson, D. J. Wil-
liams, J. Chem. Soc., Chem. Commun. 1994, 569–570.
H. Siebert, Z. Anorg. Allg. Chem. 1954, 275, 225–240.
K. Nakamoto, Infrared and Raman Spectra of Inorganic and
Coordination Compounds, Part A: Theory and Applications in
Inorganic Chemistry, 5th ed., John Wiley, New York, 1997, pp.
189–201.
[39]
[40]
[41]
[42]
[43]
[44]
[45]
[46]
[15] F. W. B. Einstein, B. R. Penfold, Acta Crystallogr. 1964, 17,
[47]
[48]
1127–1133.
[16] M. Hashimoto, T. Ozeki, H. Ichida, Y. Sasaki, K. Matsumoto,
T. Kudo, Chem. Lett. 1987, 1873–1876.
[17] R. Stomberg, Acta Chem. Scand. Ser. A 1985, 39, 507–514.
[18] L. Trysberg, R. Stomberg, Acta Chem. Scand. Ser. A 1981, 35,
823–825.
[19] I. Persdotter, L. Trysberg, R. Stomberg, Acta Chem. Scand.
Ser. A 1986, 40, 1–7.
[20] L. Salles, F. Robert, V. Semmer, Y. Jeannin, J.-M. Brégeault,
Bull. Soc. Chim. Fr. 1996, 133, 319–328.
[49]
[50]
[51]
[52]
C. Rocchiccioli-Deltcheff, M. Fournier, R. Franck, R. Thou-
venot, Inorg. Chem. 1983, 22, 207–216.
J.-M. Brégeault, G. Chottard, unpublished results.
[21] M. Hashimoto, T. Iwamoto, H. Ichida, Y. Sasaki, Polyhedron
1991, 10, 649–651.
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