Stefano Paganelli et al.
COMMUNICATIONS
0.81 (t, 9H, J=6.6 Hz), 1.20–1.35 (m, 30H), 1.60 (br, 6H),
3.20 (s, 3H), 3.30 (m, 6H); 13C NMR (75 MHz, CDCl3): d=
14.0, 22.3, 22.5, 26.3, 28.9, 29.0, 31.6, 52.2, 61.2.
[6] F. Favre, H. Olivier-Bourbigou, D. Commereuc, L.
Saussine, Chem. Commun. 2001, 1360–1361.
[7] C. P. Mehnert, R. A. Cook, N. C. Dispenziere, M. Afe-
worki, J. Am. Chem. Soc. 2002, 124, 12932–12933; A.
Riisager, P. Wasserscheid, R. van Hal, R. Fehrmann, J.
Catal. 2003, 219, 452–455.
Triphasic HydroformylationCatalysed by RhCl
3
To a glass tube containing TOMAC (1.0 mL) and H2O
(4.0 mL), RhCl3 (0.1 mmol) was added and stirred until
complete dissolution in the TOMAC phase. A solution of
olefin (1.0 mmol) in isooctane (4.0 mL) was then added to
the aqueous/ionic system. The tube was placed into a
150 mL stainless steel autoclave under nitrogen, pressurised
to 90 atm with syngas (CO/H2 =1) and heated at 60–808C
for the due time (see Table and plots). The reactor was then
cooled to room temperature and the residual gases vented.
The organic phase was separated, dried on Na2SO4 and the
reaction products characterised by GC-MS.
[8] J. P. Arhancet, M. E. Davis, J. S. Merola, B. E. Hanson,
Nature 1989, 339, 454–455; M. E. Davis, Chemtech
1992, 22, 498–502.
[9] M. Solinas, J. Jiang, O. Stelzer, W. Leitner, Angew.
Chem. Int. Ed. 2005, 44, 2291–2295.
[10] P. Tundo, A. Perosa, Chem. Soc. Rev. 2007, 36, 532–
550.
[11] P. Tundo, A. Perosa, React. Funct. Polym. 2003, 54, 95–
101.
[12] A. Perosa, P. Tundo, M. Selva, P. Canton, Chem.
Commun. 2006, 4480–4482.
[13] C. Bertucci, C. Botteghi, D. Giunta, M. Marchetti, S.
Paganelli, Adv. Synth.Catal. 2002, 344, 556–562.
[14] P. W. N. M. van Leeuwen, C. Claver, (Eds.), Rhodium
catalyzed hydroformylation, Kluwer Academic Publish-
ers, Dordrecht, 2000.
Acknowledgements
The authors wish to thank the Italian Ministry of University
and Research (MUR) for funding.
[15] J. Blum, I. Amer, A. Zoran, Y. Sasson, Tetrahedron
Lett. 1983, 24, 4139–4142.
[16] Y. Sasson, A. Zoran, J. Blum, J. Mol. Catal. 1981, 11,
293–300.
References
[17] L. Magna, Catalysis in nonaqueous ionic liquid, in:
Multiphase Homogeneous Catalysis, (Eds.: B. Cornils,
W. A. Herrmann, I. T. Horvath, W. Leitner, S. Mecking,
H. Olivier-Bourbigou, D. Vogt),Wiley-VCH, Weinheim,
2005, vol. 2, p 477.
[1] E. G. Kuntz, Chemtech 1987, 17, 570–575.
[2] B. Cornils, W. A. Herrmann, I. T. Horvath, W. Leitner,
S. Mecking, H. Olivier-Bourbigou, D. Vogt, (Eds.),
Multiphase Homogeneous Catalysis, Wiley-VCH, Wein-
heim, 2005.
[3] B. Sueur, L. Leclercq, M. Sauthier, Y. Castanet, A.
Mortreux, H. Bricout, S. Tilloy, E. Monflier, Chem.
Eur. J. 2005, 11, 6228–6236.
[18] J. P. Arhancet, M. E. Davis, J. S. Merola, B. E. Hanson,
J. Catal. 1990, 121, 327–339.
[19] T. Jefferey, Tetrahedron 1996, 52, 10113–10130.
[20] A. Haynes, B. E. Mann, G. E. Morris, P. M. Maitlis, J.
Am. Chem. Soc. 1993, 115, 4093–4100.
[4] I. T. Horvath, J. Rabai, Science 1994, 266, 72–75.
[5] P. G. Jessop, T. Ikariya, R. Noyori, Chem. Rev. 1999, 99,
475–494.
[21] K. Sato, M. Aoki, M. Ogawa, T. Hashimoto, R. Noyori,
J. Org. Chem. 1995, 61, 8310–8311.
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Adv. Synth. Catal. 2007, 349, 1858 – 1862