Accelerated biphasic hydroformylation by vesicle formation of amphiphilic diphosphines

Journal of the American Chemical Society

Volumn 122, Issue 8, 2000, Pages 1650-1657

  Goedheijt, Marcel Schreuder ^a   Hanson, Brian E ^b   Reek, Joost N H ^a   Kamer, Paul C J ^a   Van Leeuwen, Piet W N M ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHINE DERIVATIVE; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

EID: 0034058389     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9925610     Document Type: Article

References (56)

1. Cornils, B.; Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds; Wiley-VCH: Weinheim, 1996.
2. Herrmann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524.
3. Fell, B.; Schobben, C.; Papadogianakis, G. J. Mol. Catal. 1995, 101, 179.
4. Buhling, A.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Elgersma J. W., J. Mol. Catal. 1997, 116, 297.
5. (a) Cornils, B.; Herrmann, W. A. Aqueous-Phase Organometallic Chemistry -Concepts and Applications; Wiley-VCH: Weinheim, 1998.
6. (b) Cornus, B. Org. Process Res. Dev. 1998, 2, 121.
7. (a) Monteil, F.; Queau, R.; Kalck, P. J. Organomet. Chem. 1994, 480, 177.
8. (b) Buriak, J. M.; Osborn, J. A. Organometallics 1996, 15, 3161.
9. (c) Selke, R.; Ohff, M.; Riepe, A. Tetrahedron 1996, 52, 15079.
10. (a) Ding, H.; Hanson, B. E. J. Mol. Catal. 1995, 99, 131.
11. (b) Bartik, T.; Ding, H.; Bartik, B.; Hanson, B. E. J. Mol. Catal. 1995, 98, 117.
12. Fremy, G.; Monflier, E.; Carpenter, J. F.; Castanet, Y.; Mortreux, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1474.
13. Horváth, I. T.; Rábai, J. Science 1994, 266, 72.
14. Arhancet, J. P.; Davis, M. E.; Merola, J. S.; Hanson, B. E. Nature 1989, 339, 454.
15. (a) Breslow, R.; Rideout, D. C. J. Am. Chem. Soc. 1980, 102, 7816.
16. (b) Breslow, R.; Guo, T. J. Am. Chem. Soc. 1988, 110, 5613.
17. (c) Otto, S.; Boccaletti, G.; Engberts, J. B. F. N. J. Am. Chem. Soc. 1998, 120, 4238.
18. Ding, H.; Hanson, B. E.; Bartik, T.; Bartik, B. Organometallics 1994, 13, 3761.
19. (b) Hanson, B. E.; Ding, H.; Kohlpaintner, C. W. Catal. Today 1998, 42, 421.
20. (c) Oehme, G.; Grassert, I.; Ziegler, S.; Meisel, R.; Fuhrmann, H. Catal. Today 1998, 42, 459.
21. (d) Ding, H.; Hanson, B. E.; Bakos, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1645.
22. Christian, S. D.; Scamehorn, J. F. Solubilization in Surfactant Aggregates; Marcel Dekker: New York, 1995.
23. Parshall, G. W. Homogeneous Catalysis: the applications and chemistry of catalysis by soluble transition metal complexes; Wiley: New York, 1980.
24. (a) Moasser, B.; Gladfelter, W. L.; Roe, D. C. Organometallics 1995, 14, 3832.
25. (b) van Rooy, A.; Orij, E. N.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 1995, 14, 34.
26. (a) Broussard, M. E.; Juma, B.; Train, S. G.; Peng, W. J.; Laneman, S. A.; Stanley, G. G. Science 1993, 260, 1784.
27. (b) Matthews, R. C.; Howell, D. K.; Peng, W. J.; Train, S. G.; Treleaven, W. D.; Stanley, G. G. Angew. Chem., Int. Eng. Ed. 1996, 35, 2253.
28. (a) Casey, C. P.; Whiteker, G. T.; Melville, M. G.; Petrovich, L. M.; Gavney, J. A. Jr.; Powell, D. R. J. Am. Chem. Soc. 1992, 114, 5535.
29. (b) Casey, C. P.; Petrovich, L. M. J. Am. Chem. Soc. 1995, 117, 6007.
30. (c) Casey. C. P.; Paulsen, E. L.; Beuttenmueller, E. W.; Proft, B. R.; Petrovich, L. M.; Matter, B. A.; Powell, D. R. J. Am. Chem. Soc. 1997, 119, 11817.
31. (a) Kranenburg, M.; van der Burgt, Y. E. M.; Karner, P. C. J.; van Leeuwen, P. W. N. M. J. Organometallics 1995, 14, 3081.
32. (b) van der Veen, L. A.; Boele, M. D. K.; Bregman, F. R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goubitz, K.; Fraanje, J.; Schenk, H.; Bo, C. J. Am. Chem. Soc. 1998, 120, 1161.
33. (c) Kamer, P. C. J.; Reek, J. N. H.; van Leeuwen, P. W. N. M. CHEMTECH 1998, September, 27.
34. Schreuder Goedheijt, M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Mol. Catal. 1998, 134, 243.
35. (a) Adamson, A. W. In Physical Chemistry of Surfaces; Wiley-Interscience: 1990; p 509.
36. (b) Kabanov, A. V.; Bronich, T. K.; Kabanov, V. A.; Yu, K.; Eisenberg, A. J. Am. Chem. Soc. 1998, 120, 9941.
37. (a) Kunitake, T. Angew. Chem., Int. Ed. Engl. 1992, 31, 709.
38. (b) Fuhrhop, J.-H.; Mathieu, J. Angew. Chem., Int. Ed. Engl. 1984, 23, 100.
39. (c) Ringsdorf, H.; Schlarb, B. Venzmer, J. Angew. Chem., Int. Ed. Engl. 1988, 27, 7, 113.
40. A few examples: (a) Bandyopadhyay, P.; Bharadwai, P. K. Langmuir 1998, 14, 7537. (b) Ghosh, P.; Khan, T. K.; Bharadwai, P. K. Chem. Commun. 1996, 189. Kimizuka, N.; Wakiyama, T.; Miyauchi, H.; Yoshimi, T.; Tokuhiro, M.; Kunitake, T. J. Am. Chem. Soc. 1996, 118, 5808. Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, T. J. Am. Chem. Soc. 1998, 120, 4094. (e) Kabanov, A. V.; Bronich, T. K.; Kabanov, K.; Eisenberg, S. Kimizuka, N.; Wakiyama, T.; Miyauchi, H.; Yoshimi, T.; Tokuhiro, M.; Kunitake, T. J. Am. Chem. Soc. 1998, 120, 9941.
41. A few examples: (a) Bandyopadhyay, P.; Bharadwai, P. K. Langmuir 1998, 14, 7537. (b) Ghosh, P.; Khan, T. K.; Bharadwai, P. K. Chem. Commun. 1996, 189. Kimizuka, N.; Wakiyama, T.; Miyauchi, H.; Yoshimi, T.; Tokuhiro, M.; Kunitake, T. J. Am. Chem. Soc. 1996, 118, 5808. Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, T. J. Am. Chem. Soc. 1998, 120, 4094. (e) Kabanov, A. V.; Bronich, T. K.; Kabanov, K.; Eisenberg, S. Kimizuka, N.; Wakiyama, T.; Miyauchi, H.; Yoshimi, T.; Tokuhiro, M.; Kunitake, T. J. Am. Chem. Soc. 1998, 120, 9941.
42. A few examples: (a) Bandyopadhyay, P.; Bharadwai, P. K. Langmuir 1998, 14, 7537. (b) Ghosh, P.; Khan, T. K.; Bharadwai, P. K. Chem. Commun. 1996, 189. Kimizuka, N.; Wakiyama, T.; Miyauchi, H.; Yoshimi, T.; Tokuhiro, M.; Kunitake, T. J. Am. Chem. Soc. 1996, 118, 5808. Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, T. J. Am. Chem. Soc. 1998, 120, 4094. (e) Kabanov, A. V.; Bronich, T. K.; Kabanov, K.; Eisenberg, S. Kimizuka, N.; Wakiyama, T.; Miyauchi, H.; Yoshimi, T.; Tokuhiro, M.; Kunitake, T. J. Am. Chem. Soc. 1998, 120, 9941.
43. A few examples: (a) Bandyopadhyay, P.; Bharadwai, P. K. Langmuir 1998, 14, 7537. (b) Ghosh, P.; Khan, T. K.; Bharadwai, P. K. Chem. Commun. 1996, 189. Kimizuka, N.; Wakiyama, T.; Miyauchi, H.; Yoshimi, T.; Tokuhiro, M.; Kunitake, T. J. Am. Chem. Soc. 1996, 118, 5808. Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, T. J. Am. Chem. Soc. 1998, 120, 4094. (e) Kabanov, A. V.; Bronich, T. K.; Kabanov, K.; Eisenberg, S. Kimizuka, N.; Wakiyama, T.; Miyauchi, H.; Yoshimi, T.; Tokuhiro, M.; Kunitake, T. J. Am. Chem. Soc. 1998, 120, 9941.
44. A few examples: (a) Bandyopadhyay, P.; Bharadwai, P. K. Langmuir 1998, 14, 7537. (b) Ghosh, P.; Khan, T. K.; Bharadwai, P. K. Chem. Commun. 1996, 189. Kimizuka, N.; Wakiyama, T.; Miyauchi, H.; Yoshimi, T.; Tokuhiro, M.; Kunitake, T. J. Am. Chem. Soc. 1996, 118, 5808. Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, T. J. Am. Chem. Soc. 1998, 120, 4094. (e) Kabanov, A. V.; Bronich, T. K.; Kabanov, K.; Eisenberg, S. Kimizuka, N.; Wakiyama, T.; Miyauchi, H.; Yoshimi, T.; Tokuhiro, M.; Kunitake, T. J. Am. Chem. Soc. 1998, 120, 9941.
45. Lasic, D. D. J. Colloid Interface Sci. 1990, 140, 302.
46. Kalyanasundaram, K.; Thomas, J. K. J. Am. Chem. Soc. 1977, 99, 2039.
47. (a) Stam, van J.; Depaemelaere, S.; De Schryver, F. C. J. Chem. Educ. 1998, 75, 93.
48. (b) Damas, C.; Naejus, R.; Coudert, R.; Frochot, C.; Brembilla, A.; Viriot, M.-L. J. Phys. Chem. B 1998, 102, 10917.
49. Fendler, J. H.; Fendler, E. J. Catalysis in Micellar and Macromolecular Systems; Academic Press: New York, 1975.
50. (a) Lissi, E. A.; Abuin, E.; Saez, M.; Zanocco, A.; Disalvo, A. Langmuir 1992, 8, 348.
51. (b) Morris, D. A. N.; McNeil, R.; Castellino, Thomas, J. K. Biochim. Biophys. Acta 1980, 599, 380.
52. Tascioglu, S. Tetrahedron 1996, 11113.
53. (a) van der Veen, L. A.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 1999, 18, 4765.
54. (b) van der Veen, L. A.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Angew. Chem., Int. Ed. 1999, 38, 336.
55. Bartik, T.; Bartik, B.; Hanson, B. E.; Glass, T.; Behout, W. Inorg. Chem. 1992, 31, 2667.
56. Hallman, P. S.; Evans, D.; Osborn, J. A.; Wilkinson, G. Chem. Commun. 1967, 305.