Selectivity for the methoxycarbonylation of ethylene versus CO-ethylene copolymerization with catalysts based on C4-bridged bidentate phosphines and phospholes

Journal of Organometallic Chemistry

Volumn 640, Issue 1-2, 2001, Pages 182-196

  Doherty, Simon ^a   Robins, Edward G ^a   Knight, Julian G ^b   Newman, Colin R ^b   Rhodes, Barrie ^b   Champkin, Paul A ^b   Clegg, William ^b  

^a QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

^b NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

Carbon monoxide; Copolymerization; Diphosphines; Ethylene; Methoxycarbonylation; Selectivity

Indexed keywords

EID: 0038417249     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(01)01180-9     Document Type: Article

References (68)

1. Tsuji J. Palladium Reagents and Catalysts. Innovations in Organic Synthesis. 1995;Wiley, New York.
2. Chardarin C.G., Wov S.L., Clark R.C., Hathcock C.H. Tetrahedron Lett. 1976;1769.
3. Murray T.F., Samsel E.G., Varma V., Norton J.R. J. Am. Chem. Soc. 193:1981;7520.
4. Murray T.F., Varma V., Norton J.R. J. Org. Chem. 43:1978;353.
5. El Ali B., Alper H. J. Org. Chem. 56:1991;5357.
6. Alper H., Hamel N. J. Am. Chem. Soc. 112:1990;2803.
7. Houssame S.E., Firdoussi L.E., Allaoud S., Karim A., Castanet Y., Mortreux A. J. Mol. Catal. A. 168:2001;15.
8. Firdoussi L.E., Bagga A., Allaoud S., Ait Allal B., Karim A., Castanet Y., Mortreux A. J. Mol. Catal. A. 135:1998;11.
9. Drent E., Budzelaar P.H.M. Chem. Rev. 96:1996;663.
10. Sen A. Acc. Chem. Res. 26:1993;303.
11. Nozaki K., Hiyama T. J. Organomet. Chem. 576:1999;248.
12. Milani B., Mestroni G. Comments Inorg. Chem. 20:1999;301.
13. Sperrle M., Consiglio G. Chem. Ber. 130:1997;1557.
14. Vavasori A., Toniolo L. J. Mol. Catal. A. 110:1996;13.
15. Drent E., van Broekhoven J.A.M., Budzelaar P.H.M. Cornils B., Hermann W.A. Applied Homogeneneous Catalysis with Organometallic Compounds. 1:1996;VCH, Weinheim. (333 pp.).
16. E. Drent, Eur. Patent Appl., EP 0 495 548 (1992);
17. E. Drent, Eur. Patent Appl., EP 0 495 547 (1992);
18. E. Drent, Eur. Patent Appl., WO 97/03943 (1997);
19. G.R. Eastham, R.P. Tooze, X.L. Wang, K. Whiston, (ICI) WO 96/19434 (1996);
20. Parshall G.W., Ittel S.D. Homogeneous Catalysis: The Applications and Catalysis by Soluble Transition Metal Complexes. 1992;Wiley, New York.
21. For examples of diphosphines see: (a) E. Drent, Eur. Pat. Appl. 121 965 A2, 1984;
22. (b) E. Drent, J.A.M. van Broekhoven, M.J. Doyle, J. Organomet. Chem. 417 (1991) 235;
23. (c) M. Barsacchi, A. Batistini, G. Consiglio, U.W. Suter, Macromolecules 25 (1992) 3604;
24. (d) M. Sperrles, G. Consiglio, J. Am. Chem. Soc. 117 (1995) 12130;
25. (e) Z. Jiang, S.E. Adams, A. Sen, Macromolecules 27 (1994) 2694;
26. (f) Z. Jiang, A. Sen, J. Am. Chem. Soc. 117 (1995) 4455;
27. (g) C. Bianchini, H.M. Lee, A. Meli, S. Moneti, F. Vizza, M. Fontani, P. Zanello, Macromolecules 32 (1999) 4183;
28. (h) C. Bianchini, H.M. Lee, A. Meli, W. Oberhauser, F. Vizza, P. Bruggeller, R. Haid, C. Langes, Chem. Commun. (2000) 777;
29. (i) G. Verspini, F. Schanserra, R.A. Sheldon, Angew. Chem. Int. Ed. Engl. 39 (2000) 803; For examples of dintrogen donors see:
30. (j) F.C. Rix, M. Brookhart, P.S. White, J. Am. Chem. Soc. 118 (1996) 4746;
31. (k) B. Milani, A. Anzilutti, L. Vicentini, A. Sessanta Santi, E. Zangrando, S. Geremia, G. Mestroni, Organometallics 16 (1997) 5064;
32. (l) B.A. Markies, D. Kruis, M.H.P. Rietveld, K.A.N. Verberk, J. Boersma, H. Koojima, M.T. Lakin, A.L. Speck, G. van Koten, J. Am. Chem. Soc. 117 (1995) 117, 5263;
33. (m) M. Brookhart, F.C. Rix, J.M. DeSimone, J.C. Barborak, J. Am. Chem. Soc. 114 (1992) 5894;
34. (n) M. Brookhart, M.I. Wagner, G.G.A. Balavoine, H.A. Haddou, J. Am. Chem. Soc. 1126 (1994) 3641;
35. (o) B. Milani, L. Vicentini, A. Sonmazzi, F. Garbassi, E. Chiarparin, E. Zangrando, G. Mestroni, J. Chem. Soc. Dalton Trans. (1996) 3139;
36. (p) B. Milani, E. Alessio, G. Mestroni, E. Zangrando, L. Randaccio, G. Consiglio, J. Chem. Soc. Dalton Trans. (1996) 1021;
37. (q) M. Brookhart, M.I. Wagner, J. Am. Chem. Soc. 118 (1996) 7219;
38. (r) L.K. Johnson, S. Mecking, M. Brookhart, J. Am. Chem. Soc. 118 (1996) 267.
39. Clegg W., Eastham G.R., Elsegood M.R.J., Tooze R.P., Wang X.L., Whiston K. Chem. Commun. 1999;1877.
40. Eastham G.R., Heaton B.T., Iggo J.A., Tooze R.P., Whyman R., Zucchini S. Chem. Commun. 2000;609.
41. Tooze R.P., Whiston K., Malyan A.P., Taylor M.J., Wilson N.W. J. Chem. Soc. Dalton Trans. 2000;3441.
42. Seayad A., Jayasree S., Damodarao K., Toniolo L., Chaudhari R.V. J. Organomet. Chem. 601:2001;100.
43. Doherty S., Eastham G.R., Tooze R.P., Scanlan T.S., Williams D., Elsegood M.R.J., Clegg W. Organometallics. 18:1999;3558.
44. Knight J.G., Doherty S., Harriman A., Robins E.G., Betham M., Eastham G.R., Tooze R.P., Elsegood M.R.J., Champkin P., Clegg W. Organometallics. 19:2000;4957.
45. Weinges K., Sipos W., Klein J., Deuter J., Irngartinger H. Chem. Ber. 120:1987;5.
46. Fagan P.J., Nugent W.A., Calabrese J.C. J. Am. Chem. Soc. 116:1994;1880.
47. Sheldrick G.M. SHELXTL User Manual, Version 5. 1994;Bruker AXS Inc, Madison, WI.
48. SMART and SAINT software for CCD diffractometers, Bruker AXS Inc., Madison, WI, 1994.
49. Gradoz P., Baudry D., Ephritikhine M., Nief F., Mathey F. J. Chem. Soc. Dalton Trans. 1992;3047.
50. MacDougall J.J., Nelson J.H., Mathey F., Mayerle J. J. Inorg. Chem. 19:1980;709.
51. Stephenson T.A., Morehouse S.M., Powell A.R., Heffer J.P., Wilkinson G. J. Chem. Soc. 1965;3632.
52. Gougygou M., Tissot O., Daran J.-C., Balavoine G.G.A. Organometallics. 16:1997;1008.
53. MacDougall J.J., Nelson J.H., Mathey F., Mayerle J.J. Inorg. Chem. 19:1980;709.
54. Kojima T., Saeki K., Ono K., Ohba M., Matsuda Y. Chem. Commun. 1997;1697.
55. Wilson W.L., Fischer J., Wasylishen R.E., Eichele K., Catalano V.J., Frederick J.H., Nelson J.H. Inorg. Chem. 35:1996;1486.
56. Gul N., Nelson J.H. Tetrahedron. 26:2000;71.
57. Gul N., Nelson J.H. Organometallics. 19:2000;91.
58. Makhaev V.D., Dzhabieva Z.M., Konovalikhin S.V., D'Yachenko O.A., Belov G.P. Koord. Khim. 22:1996;598.
59. Gramlich V., Consiglio G. Helv. Chim. Acta. 62:1979;1016.
60. Hayashi T., Konishi M., Kabori Y., Kumada M., Higuchi T., Mirotsu K. J. Am. Chem. Soc. 106:1984;158.
61. Dossett S.J., Gillon A., Orpen A.G., Fleming J.S., Pringle P.G., Wass D.F., Jones M.D. Chem. Commun. 2001;699.
62. Barlow G.K., Boyle J.D., Cooley N.A., Ghaffar T., Wass D.F. Organometallics. 19:2000;1470.
63. Dierkes P., van Leeuwen P.W.M.N. J. Chem. Soc. Dalton Trans. 1999;1519.
64. Sanger A.R. J. Chem. Soc. Dalton Trans. 1977;1971.
65. Consiglio G., Nefkens C.A.S. Tetrahedron: Asymmetry. 1:1990;417.
66. Portnoy M., Ben-David Y., Milstein D. J. Organomet. Chem. 503:1995;149.
67. Dekker G.P.C.M., Elsevier C.J., Vrieze K., van Leeuwen P.W.M.N. Organometallics. 11:1992;1598.
68. Al-Salem N.A., Empsall H.D., Markham R., Shaw B.L., Weeks B. J. Chem. Soc. Dalton Trans. 1979;1972.