Michel Picquet et al.
COMMUNICATIONS
2008C) with methyl benzoate as internal standard is performed
in duplicate.
[8] a) Christie, S. Subramanian, L. Wang, M. J. Zaworotko,
Inorg. Chem. 1993, 32, 5415; b) J. D. Holbrey, K. R.
Seddon, J. Chem. Soc., Dalton Trans. 1999, 2133.
[9] H. Ohno, M. Yoshizawa, Solid State Ionics 2002,
154 155, 303.
General Procedure: RCM of N,N-Diallyltosylamide
(Table 2)
[10] a) P. Grenouillet, D. Neibecker, I. Tkatchenko, French
√
Patent 2,596,390 (Rhone-Poulenc, 10.02.1987); b) P.
In a Schlenk tube are successively placed under argon and
agitation (magnetic bar) the imidazolium salt (4 mmol, 400
equiv.) and N,N-diallyltosylamide (0.5 mmol, 50 equiv.). The
mixture is stirred 10 min at room temperature to obtain a
Grenouillet, D. Neibecker, I. Tkatchenko, US Patent
√
4,889,949 (Rhone-Poulenc, 26.12.1989); c) P. Grenouillet,
D. Neibecker, I. Tkatchenko, Organometallics, 1984, 3,
1130.
colourless homogeneous liquid then [Ru( C C CPh2)-
[11] M. Picquet, S. Stutzmann, I. Tkatchenko, I. Tommasi, P.
Wasserscheid, J. Zimmermann, Green Chemistry 2003, 5,
153.
[12] P. A. Z. Suarez, J. E. L. Dullius, S. Einloft, R. F. de Sou-
za, J. Dupont, Polyhedron 1996, 15, 1217.
(p-cymene)(PCy3)Cl][OTf] (0.01 mmol, 1 equiv., 2 mol %) is
added. The red to violet solution is placed at 34 to 508C for
15 min then cooled to room temperature. The conversion is
1
determined by H NMR of the crude reaction mixture. The
product is isolated by simple extraction with Et2O (3 Â 10 mL).
[13] J. Zimmermann, P. Wasserscheid, I. Tkatchenko, S.
Stutzmann, Chem. Commun. 2002, 760.
[14] I. Guibert, D. Neibecker, I. Tkatchenko, J. Chem. Soc.,
Chem. Commun. 1989, 1850.
Acknowledgements
[15] D. S. McGuiness, K. J. Cavell, B. F. Yates, B. W. Skelton,
A. H. White, J. Am. Chem. Soc. 2001, 123, 8317.
[16] S. Gr¸ndemann, M. Albrecht, A. Kovacevic, J. W. Faller,
R. H. Crabtree, J. Chem. Soc., Dalton Trans. 2002, 2163.
[17] M. Brookhart, S. Sabo-Etienne, J. Am. Chem. Soc. 1991,
113, 2777.
¬
We acknowledge CNRS and Universite de Bourgogne for
continuous support. ITo thanks Region Bourgogne for a post-
doctoral fellowship.
¬
[18] M. S. Sanford, L. H. Henling, R. H. Grubbs, Organo-
metallics 1998, 17, 5384.
References and Notes
[19] D. M. Lynn, B. Mohr, R. H. Grubbs, L. H. Henling,
M. W. Day, J. Am. Chem. Soc. 2000, 122, 6601.
[20] A. F¸rstner, M. Liebl, C. W. Lehmann, M. Picquet, R.
Kunz, C. Bruneau, P. H. Dixneuf, Chem. Eur. J. 2000, 6,
1847.
[21] a) C. G¸rtler, M. Jautelat, Eur. Patent 1,035,093 A2
(Bayer AG, 21.02.2000); b) R. C. Buijsman, E. van Vuu-
ren, J. G. Sterrenburg, Org. Lett. 2001, 3, 3785; c) K. G.
Mayo, E. H. Nearhoof, J. J. Kiddle, Org. Lett. 2002, 4,
1567.
[z] Part 2: See Chem. Commun. 2003, 28 29.
[1] a) M. Coax, J. Chem. Technol. Biotechnol. 1997, 68, 351;
b) J. D. Holbrey, K. R. Seddon, Clean Prod. Processes
1999, 1, 223; c) T. Welton, Chem. Rev. 1999, 99, 2071; d) J.
Dupont, R. F. de Souza, P. A. Z. Suarez, Chem. Rev.
2002, 102, 3667.
[2] a) P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed.
2000, 39, 3772 3789; b) R. A. Sheldon, Chem. Commun.
2001, 2399.
¡
¬
[3] A. Bˆsmann, G. Francio, E. Janssen, M. Solinas, W.
[22] a) D. Semeril, H. Olivier-Bourbigou, C. Bruneau, P. H.
Leitner, P. Wasserscheid, Angew. Chem. Int. Ed. 2001, 40,
2697.
Dixneuf, Chem. Commun. 2002, 146; b) S. Csihony, C.
¬
Fischmeister, C. Bruneau, I. T. Horvath, P. H. Dixneuf,
[4] a) Y. Chauvin, B. Gilbert, I. Guibard, J. Chem. Soc.
Chem. Commun. 1990, 1715; b) Y. Chauvin, H. Bourbi-
gou, Chemtech 1995, (9), 26.
New J. Chem. 2002, 26, 1667.
[23] V. K. Aggarwal, I. Emme, A. Mereu, Chem. Commun.
2002, 1612.
[5] B. M. Trost, Chem. Eur. J. 1998, 4, 2405.
[6] C. K. Lee, H. W. Hunag, I. J. N. Lin, J. Chem. Soc. Chem.
Commun. 2000, 1911.
[24] J. Herwig, Applied Homogeneous Catalysis with Organo-
metallic Compounds, Vol. 3 (Eds.: B. Cornils, W. A.
Herrmann), Wiley-VCH, Weinheim, 2nd edn., 2002,
p. 694.
[7] K. K. Laali, V. J. Gettwert, J. Org. Chem. 2001, 66, 35.
962
¹ 2003 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
asc.wiley-vch.de
Adv. Synth. Catal. 2003, 345, 959 962