C. Bibal et al. / Polyhedron 29 (2010) 639–647
647
[10] (a) F.E. Kühn, A.M. Santos, A.D. Lopes, I.S. Gonçalves, J.E. Rodríguez-Borges, M.
Pillinger, C.C. Romão, J. Organomet. Chem. 621 (2001) 207;
(b) F.E. Kühn, A.D. Lopes, A.M. Santos, E. Herdtweck, J.J. Haider, C.C. Romão,
A.G. Santos, J. Mol. Catal. A: Chem. 151 (2000) 147;
Utilization of recycled catalyst showed similar activity in the
second cycle. To our surprise we found for compound 3 in the sec-
ond run even a slightly bigger activity relative to the first cycle.
This is likely due to difficulties in the experimental procedure, re-
lated to the low solubility of catalyst 3 in the reaction media. Pre-
viously, we obtained an 86% yield of epoxide for this reaction (see
above). After three consecutive reactions, the catalytic activity de-
creased significantly to yield only 38% of cyclooctene oxide, prob-
ably due to incremental metal loss during the extraction processes.
The fifth and final cycle yielded only 19% of cyclooctene oxide. The
recycling performance of 3 is comparable to other previously pub-
lished MoVI catalysts [13a,13b].
(c) A.A. Valente, I.S. Rodríguez-Borges, M. Pillinger, C.C. Romão, J. Rocha, X.
García-Mera, New J. Chem. 25 (2001) 959;
(d) J. Fridgen, W.A. Herrmann, G. Eickerling, A.M. Santos, F.E. Kühn, J.
Organomet. Chem. 689 (2004) 2752;
(e) A. Al-Ajlouni, A.A. Valente, C.D. Numes, M. Pillinger, A.M. Santos, J. Zhao,
C.C. Romão, I.S. Rodríguez-Borges, F.E. Kühn, Eur. J. Inorg. Chem. (2005) 1716.
[11] (a) Y.-L. Wong, Y. Yan, E.S.H. Chan, Q. Yang, T.C.W. Mak, D.K.P. Ng, J. Chem.
Soc., Dalton Trans. (1998) 3057;
(b) X.-Y. Wang, H.-C. Shi, C. Suan, C. Sun, Z.-G. Zhang, Tetrahedron 60 (2004)
10993;
(c) S.M. Bruno, S.S. Baluta, A.A. Valente, F.A. Almeida Paz, M. Pillinger, C. Sousa,
J. Klinowski, C. Freire, P. Ribeiro-Claro, I.S. Gonçalves, J. Mol. Catal. A: Chem.
270 (2007) 185.
[12] (a) Y. Sui, X. Zeng, X. Fang, X. Fu, Y. Xiao, L. Chen, M. Li, S. Cheng, J. Mol. Catal.
A: Chem. 270 (2007) 61;
4. Conclusion
(b) J.M. Sobczak, J.J. Ziółkowski, Appl. Catal. A. 248 (2003) 261;
(c) J. Zhao, X. Zhou, A.M. Santos, E. Herdtweck, C.C. Romão, F.E. Kühn, Dalton
Trans. (2003) 3736;
Diprotic anionic sulfonated Schiff bases (of ‘‘ONO”-type) have
been assembled by straightforward synthetic procedures that
allow the facile introduction of different motifs on the imine func-
tion. The corresponding sulfonated Schiff base dioxidomolybde-
num complexes have been easily prepared by reaction with the
MoO2(acac)2 precursor. They have been engaged in the cyclooctene
epoxidation in IL media with TBHP as oxidant. The best catalytic
systems are the salts of N-salicylidene-2-aminophenolate sulfo-
(d) X. Zhou, J. Zhao, A.M. Santos, F.E. Kühn, Z. Naturforsch. Teil
B
(2004) 1223.
ˇ
[13] (a) A.A. Valente, Z. Petrovski, L.C. Branco, C.A.M. Afonso, M. Pillinger, A.D.
Lopes, C.C. Romão, C.D. Nunes, I.S. Gonçalves, J. Mol. Catal. A: Chem. 218 (2004)
5;
(b) F.E. Kühn, J. Zhao, M. Abrantes, W. Sun, C.A.M. Afonso, L.C. Branco, I.S.
Gonçalves, M. Pillinger, C.C. Romão, Tetrahedron Lett. 46 (2005) 47;
(c) M. Herbert, A. Galindo, F. Montilla, Catal. Commun. 8 (2007) 987.
[14] (a) F.E. Kühn, M. Goarke, E. Bencze, E. Herdweck, A. Prazeres, A.M. Santos, M.J.
Calhorda, C.C. Romao, I.S. Gonçalves, A.D. Lopes, M. Pillinger, Chem. Eur. J. 8
(2002) 2370;
(b) R.A. Sheldon, J.K. Kochi, Adv. Catal. 25 (1976) 272.
[15] O.A. Rajan, A. Chakravorty, Inorg. Chem. 20 (1981) 660.
[16] G.W. Kirker, Prep. Proced. Int. 12 (1980) 246.
[17] A. Altomare, M.C. Burla, M. Camalli, G.L. Cascarano, C. Giacovazzo, A.
Guagliardi, A.G.G. Moliterni, G. Polidori, R. Spagna, J. Appl. Crystallogr. 32
(1999) 115.
[18] G.M. Sheldrick, SHELXL97, Program for Crystal Structure Refinement. University
of Göttingen, Germany, 1997.
nate dioxidomolybdenum(VI),
3 and 5, in the ionic liquid
[BMIM][NTf2]. We showed that in the case of catalyst 3 in
[BMIM][NTf2], the IL phase along with the immobilized catalyst
can be reused for at least three runs with a fairly comparable cat-
alytic activity.
Appendix A. Supplementary data
[19] L.J. Farrugia, J. Appl. Crystallogr. 30 (1997) 565.
[20] (a) K.H. Walter, Chem. Ber. 95 (1962) 777;
CCDC 727532, 727533 and 727534 contain the supplementary
crystallographic data for [HOCH2CH2NH3][H2sSAE], 3 and 5. These
Data Center, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44)
1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk. Supplementary
data associated with this article can be found, in the online version,
(b) D.F. Evans, D.A. Jakubovic, Polyhedron 7 (1988) 1881;
(c) D.F. Evans, D.A. Jakubovic, Polyhedron 7 (1988) 2723;
(d) S. Dutta, A. Chakravorty, Polyhedron 13 (1994) 1811.
[21] (a) D. Chen, A.E. Martell, Y. Sun, Inorg. Chem. 28 (1989) 2647;
(b) D.M. Boghaei, M. Gharagozlou, J. Coord. Chem. 60 (2007) 339.
[22] (a) C.P. Rao, A. Sreedhara, P.V. Rao, M.B. Verghese, K. Rissanen, E. Kolehmainen,
N.K. Lokanath, M.A. Sridhar, J.S. Prasad, J. Chem. Soc., Dalton Trans. (1998)
2383;
(b) H.R. Holm, Chem. Rev. 87 (1987) 1401.
[23] J.A. Craig, E.W. Harlan, B.S. Snyder, M.A. Whitener, R.H. Holm, Inorg. Chem.
(1989) 2808.
[24] F.H. Allen, O. Kennard, D.G. Watson, L. Brammer, A.G. Orpen, R. Taylor, J. Chem.
Soc., Perkin Trans. 1 2 (1987) S1.
[25] (a) H. Karabiyik, B. Güzel, M. Aygün, G. Bog˘a, O. Büyükgüngör, Acta
Crystallogr., Sect. C 63 (2007) o215;
References
[1] (a) B. Cornils, Angew. Chem., Int. Ed. Engl. (1995) 1575;
(b) W.A. Herrmann, C.W. Kohlpaintner, Angew. Chem., Int. Ed. Engl. 32 (1993)
1524;
(b) K. Ogawa, J. Harada, J. Mol. Struct. 647 (2003) 211.
(c) K.H. Shaughnessy, Chem. Rev. 109 (2009) 643.
´
[26] W. Schilf, B. Kamienski, A. Szady-Chełmieniecka, E. Grech, J. Mol. Struct. 700
[2] (a) Y. Chauvin, S. Einloft, H. Olivier, Ind. Eng. Chem. Res. 34 (1995) 1149;
(b) Y. Chauvin, B. Gilbert, I. Guibard, J. Chem. Soc., Chem. Commun. (1990)
1715.
(2004) 105.
[27] (a) J. Topich, Inorg. Chem. 20 (1981) 3704;
(b) J.M. Sobczak, T. Głowiak, J.J. Ziółkowski, Transition Met. Chem. 15 (1990)
208;
[c] D. Agustin, C. Bibal, B. Neveux, J.-C. Daran, R. Poli, Z. Anorg. Allg. Chem. (in
[3] (a) T. Welton, Chem. Rev. 99 (1999) 2071;
(b) M.J. Earle, K.R. Seddon, Pure Appl. Chem. 72 (2000) 1391.
[4] (a) P. Wasserscheid, W. Keim, Angew. Chem., Int. Ed. 39 (2000) 3772;
(b) R. Sheldon, Chem. Commun. (2001) 2399;
(c) J. Dupont, R.F. de Souza, P.A.Z. Suarez, Chem. Rev. 102 (2002) 3667;
(d) V.I. Pârvulescu, C. Hardacre, Chem. Rev. 107 (2007) 2615.
[5] J. Muzard, Adv. Synth. Catal. 348 (2006) 275.
[6] J. Dupont, J. Spencer, Angew. Chem., Int. Ed. 43 (2004) 5296.
[7] (a) E.D. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), Comprehensive Asymmetric
Catalysis, vol. 2, Springer, Verlag, Berlin, Germany, 1999;
(b) T. Katsuki, Coord. Chem. Rev. 140 (1995) 189;
(c) T.P. Yoon, E.N. Jacobsen, Science 299 (2003) 1691;
(d) J.F. Larrow, E.N. Jacobsen, Top. Organomet. Chem. 6 (2004) 123;
(e) L. Canali, D.C. Sherrington, Chem. Soc. Rev. 28 (1999) 85.
[8] (a) C.E. Song, E.J. Roh, Chem. Commun. (2000) 837;
(b) K. Smith, S. Liu, G.A. El-Hiti, Catal. Lett. (2004) 95;
(c) L.D. Pinto, J. Dupont, R.F. de Souza, K. Bernado-Gusmao, Catal. Commmun. 9
(2008) 135.
[28] (a) S. Battacharjee, J.A. Anderson, Chem. Commun. (2004) 554;
(b) S. Battacharjee, T.J. Dines, J.A. Anderson, J. Catal. 225 (2004) 398;
(c) S. Battacharjee, J.A. Anderson, Adv. Synth. Catal. 348 (2006) 151;
(d) B.M. Choudary, T. Raman, H. Makeswaran, L. Prashant, K.V.S. Ranganath,
K.V. Kumar, Adv. Synth. Catal. 348 (2006) 493;
(e) M. Lakshimi Kantam, T. Ramani, L. Chakrapani, B.M. Choudary, J. Mol. Catal.
A: Chem. 274 (2007) 11;
(f) X. Tang, Y. Tang, G. Xu, S. Wei, Y. Sun, Catal. Commun. 10 (2008) 317;
(g) S. Battacharjee, J.A. Anderson, J. Mol. Catal. A: Chem 249 (2006) 103;
(h) S. Battacharjee, T.J. Dines, J.A. Anderson, J. Phys. Chem. C 112 (2008)
14124.
[29] (a) I. Correia, J.C. Pessoa, M.T. Duarte, M.F. Minas das Piedade, T. Jackush, T.
Kiss, M. Margarita, C.A. Castro, Carlos F.G.C. Geraldes, F. Avecilla, Eur. J. Inorg.
Chem. (2005) 732;
(b) I. Correia, A. Dornyei, T. Jakusch, F. Avecilla, T. Kiss, J.C. Pessoa, Eur. J. Inorg.
Chem. (2006) 2819.
[30] S. Liu, J. Xiao, J. Mol. Catal. A: Chem. 270 (2007) 1.
[9] (a) F.E. Kühn, J. Zhao, W.A. Herrmann, Tetrahedron: Asymmetry 16 (2005)
3469;
(b) K.R. Jain, W.A. Herrmann, F.E. Kühn, Coord. Chem. Rev. 252 (2008) 556.