Alumoxanes as cocatalysts in the palladium-catalyzed copolymerization of carbon monoxide and ethylene: Genesis of a structure-activity relationship

Organometallics

Volumn 15, Issue 9, 1996, Pages 2213-2226

  Koide, Yoshihiro ^a   Bott, Simon G ^b   Barron, Andrew R ^a  

^a RICE UNIVERSITY   (United States)

^b UNIVERSITY OF NORTH TEXAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001519093     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9508492     Document Type: Article

References (77)

1. Sen, A.; Lai, T. J. Am. Chem. Soc. 1982, 104, 3520.
2. Lai, T.; Sen, A. Organometallics 1984, 3, 866.
3. See for example: (a) Drent, E.; Wife, R. L. U.S. Patent 4,970,-294, 1990. (b) Van Leeuwen, P. W. N.; Roobeek, C. F.; Wong, P. K. Eur. Pat. Appl. EP 393,790, 1990. (c) Drent, E. Eur. Pat. Appl. EP 390,292, 1990.
4. See for example: (a) Drent, E.; Wife, R. L. U.S. Patent 4,970,-294, 1990. (b) Van Leeuwen, P. W. N.; Roobeek, C. F.; Wong, P. K. Eur. Pat. Appl. EP 393,790, 1990. (c) Drent, E. Eur. Pat. Appl. EP 390,292, 1990.
5. See for example: (a) Drent, E.; Wife, R. L. U.S. Patent 4,970,-294, 1990. (b) Van Leeuwen, P. W. N.; Roobeek, C. F.; Wong, P. K. Eur. Pat. Appl. EP 393,790, 1990. (c) Drent, E. Eur. Pat. Appl. EP 390,292, 1990.
6. See: (a) Brookhart, M.; Grant, B.; Volpe, A. F., Jr. Organometallics 1992, 11, 3920. (b) Brookhart, M.; Rix, F. C.; DeSimone, J. M.; Barborak, J. C. J. Am. Chem. Soc. 1992, 114, 5894.
7. See: (a) Brookhart, M.; Grant, B.; Volpe, A. F., Jr. Organometallics 1992, 11, 3920. (b) Brookhart, M.; Rix, F. C.; DeSimone, J. M.; Barborak, J. C. J. Am. Chem. Soc. 1992, 114, 5894.
8. Drent, E.; Van Broekhoven, J. A. M.; Doyle, M. J. J. Organomet. Chem. 1991, 417, 235.
9. Chepaikin, E. G.; Bezruchenko, A. P.; Belov, G. P. Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 9, 2181.
10. Sen, A.; Jiang, Z. Macromolecules 1993, 26, 911.
11. Klaubunde, U.; Tulip, T. H.; Roe, D. C.; Ittel, S. D. J. Organomet. Chem. 1987, 334, 141.
12. Koide, Y.; Barron, A. R. Macromolecules 1996, 29, 1110.
13. Koide, Y.; Barron, A. R. Main Group Met. Chem. 1995, 18, 405.
14. Harlan, C. J.; Bott, S. G.; Barron, A. R. J. Am. Chem. Soc. 1995, 117, 6465.
15. We have defined latent Lewis acidity to be the ability of electron-precise cage compounds to act as Lewis acids upon cage opening. The extent of latent Lewis acidity is dependent on the ring strain within the cage.
16. Mason, M. R.; Smith, J. M.; Bott, S. G.; Barron, A. R. J. Am. Chem. Soc. 1993, 115, 4971.
17. Harlan, C. J.; Mason, M. R.; Barron, A. R. Organometallics 1994, 13, 2957.
18. 100 psi = 5170 Torr = 6.89 bar.
19. Lommerts, B. J.; Mop, E. A.; Aerts, J. J. Polym. Sci., Polym. Phys. 1993, 31, 1319.
20. Polyketone, prepared from carbon monoxide and ethylene, is known to crystallize in two forms: an α- and a β-phase. There is, however, some disagreement as to the relationship of the phases. Several workers have proposed that the β-phase is a high-temperature form of the α-phase. Alternatively, it has been proposed that the change in crystal structure is due to defects in the chains introduced upon heating; see: Chatani, Y.; Takizawa, T.; Murahashi, S.; Sakata, Y.; Nishimura, Y. J. Polym. Sci. 1961, 55, 811.
21. Wu, B.; Lenz, R. W.; Harlan, C. J.; Barron, A. R. Can. J. Microbiol. 1995, 41, 274.
22. Under our conditions, there is sometimes a decrease in the polymer yield at higher alumoxane concentrations. This observation is contrary to expectations and is possibly indicative of the instability of the palladium-alumoxane complex, in the absence of ethylene/CO.
23. Poulin, J.-C.; Dang, T.-P.; Kagan, H. B. J. Organomet. Chem. 1975, 84, 87.
24. Xu, F. Y.; Zhao, A. X.; Chien, J. C. W. Makromol. Chem. 1993, 194, 2519.
25. Tolman, C. A. Chem. Rev. 1977, 77, 313.
26. tBu]Cl suitable for X-ray crystallography. Thus, the Pd-P-Ph angles and pocket angles were determined from related structures; see: (a) Haggerty, B. S.; Housecroft, C. E.; Rheingold, A. L.; Shaykh, B. A. M. J. Chem. Soc., Dalton Trans. 1991, 2175. (b) Werner, H.; Ebner, M.; Bertleff, W.; Schubert, U. Organometallics 1983, 2, 891. (c) Ganter, C.; Orpen, A. G.; Bergamini, P.; Costa, E. Acta Crystallogr., Sect. C 1994, C50, 507.
27. tBu]Cl suitable for X-ray crystallography. Thus, the Pd-P-Ph angles and pocket angles were determined from related structures; see: (a) Haggerty, B. S.; Housecroft, C. E.; Rheingold, A. L.; Shaykh, B. A. M. J. Chem. Soc., Dalton Trans. 1991, 2175. (b) Werner, H.; Ebner, M.; Bertleff, W.; Schubert, U. Organometallics 1983, 2, 891. (c) Ganter, C.; Orpen, A. G.; Bergamini, P.; Costa, E. Acta Crystallogr., Sect. C 1994, C50, 507.
28. tBu]Cl suitable for X-ray crystallography. Thus, the Pd-P-Ph angles and pocket angles were determined from related structures; see: (a) Haggerty, B. S.; Housecroft, C. E.; Rheingold, A. L.; Shaykh, B. A. M. J. Chem. Soc., Dalton Trans. 1991, 2175. (b) Werner, H.; Ebner, M.; Bertleff, W.; Schubert, U. Organometallics 1983, 2, 891. (c) Ganter, C.; Orpen, A. G.; Bergamini, P.; Costa, E. Acta Crystallogr., Sect. C 1994, C50, 507.
29. We have defined the "pocket angle" to be the interior cone angle of a chelating phosphine.
30. The pocket angles given in Table 1 are calculated from X-ray crystal structures of the palladium complexes; however, similar values are obtained by assuming a generic M-P bond distance of 2.28 Å, as is done for cone angle measurements; cf. ref 23.
31. 2 plane; see: Albright, T. A.; Hoffmann, R.; Thibeault, J. C.; Thorn, D. L. J. Am. Chem. Soc. 1979, 101, 3801. However, the ethylene must be coplanar with the acyl group for migration to occur: Hoffmann, R. J. Am. Chem. Soc. 1978, 100, 2079.
32. 2 plane; see: Albright, T. A.; Hoffmann, R.; Thibeault, J. C.; Thorn, D. L. J. Am. Chem. Soc. 1979, 101, 3801. However, the ethylene must be coplanar with the acyl group for migration to occur: Hoffmann, R. J. Am. Chem. Soc. 1978, 100, 2079.
33. (a) van Asselt, R.; Gielens, E. C. G.; Rülke, R. E.; Vrieze. K.; Elsevier, C. J. J. Am. Chem. Soc. 1994, 116, 977.
34. (b) Brumbaugh, J. S.; Whittle, R. R.; Parvez, M. A.; Sen, A. Organometallics 1990, 9, 1735.
35. Steffen, W. L.; Palenik, G. J. Inorg. Chem. 1976, 15, 2432.
36. 2; see: Ganguly, S.; Mague, J. T.; Roundhill, D. M. Acta Crystallogr., Sect. C 1994, C50, 217.
37. Ros, R.; Lenarda, M.; Pahor, N. B.; Calligaris, M.; Delise, P.; Randaccio, L.; Graziani, M. J. Chem. Soc., Dalton Trans. 1976, 1937.
38. See for example: (a) Wisner, J. M.; Bartczark, T. J.; Ibers, J. A. Organometallics 1986, 5, 2044. (b) de Graaf, W.; Boersma, J.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. Organometallics 1989, 8, 2907.
39. See for example: (a) Wisner, J. M.; Bartczark, T. J.; Ibers, J. A. Organometallics 1986, 5, 2044. (b) de Graaf, W.; Boersma, J.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. Organometallics 1989, 8, 2907.
40. See for example: (a) Lyons, D.; Wilkinson, G.; Thornton-Pett, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1984, 695. (b) Barron, A. R.; Wilkinson, G.; Motevalli, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1987, 837.
41. See for example: (a) Lyons, D.; Wilkinson, G.; Thornton-Pett, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1984, 695. (b) Barron, A. R.; Wilkinson, G.; Motevalli, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1987, 837.
42. Hermann, W. A.; Brossmer, C.; Priermeier, T.; Öfele, K. J. Organomet. Chem. 1994, 481, 97.
43. See for example: (a) Salt, J. E.; Girolami, G. S.; Wilkinson, G.; Motevalli, M.; Thornton-Pett, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1985, 685. (b) Girolami, G. S.; Wilkinson, G.; Galas, A. M. R.; Thornton-Pett, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1985, 1339. (c) Salt, J. E.; Wilkinson, G.; Motevalli, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1986, 1141. (d) Barron, A. R.; Salt, J. E.; Girolami, G. S.; Wilkinson, G.; Motevalli, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1987, 2947.
44. See for example: (a) Salt, J. E.; Girolami, G. S.; Wilkinson, G.; Motevalli, M.; Thornton-Pett, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1985, 685. (b) Girolami, G. S.; Wilkinson, G.; Galas, A. M. R.; Thornton-Pett, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1985, 1339. (c) Salt, J. E.; Wilkinson, G.; Motevalli, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1986, 1141. (d) Barron, A. R.; Salt, J. E.; Girolami, G. S.; Wilkinson, G.; Motevalli, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1987, 2947.
45. See for example: (a) Salt, J. E.; Girolami, G. S.; Wilkinson, G.; Motevalli, M.; Thornton-Pett, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1985, 685. (b) Girolami, G. S.; Wilkinson, G.; Galas, A. M. R.; Thornton-Pett, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1985, 1339. (c) Salt, J. E.; Wilkinson, G.; Motevalli, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1986, 1141. (d) Barron, A. R.; Salt, J. E.; Girolami, G. S.; Wilkinson, G.; Motevalli, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1987, 2947.
46. See for example: (a) Salt, J. E.; Girolami, G. S.; Wilkinson, G.; Motevalli, M.; Thornton-Pett, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1985, 685. (b) Girolami, G. S.; Wilkinson, G.; Galas, A. M. R.; Thornton-Pett, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1985, 1339. (c) Salt, J. E.; Wilkinson, G.; Motevalli, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1986, 1141. (d) Barron, A. R.; Salt, J. E.; Girolami, G. S.; Wilkinson, G.; Motevalli, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1987, 2947.
47. (a) Jiang, Z.; Dahlen, G. M.; Houseknecht, K.; Sen, A. Polym. Prepr., Am. Chem. Soc., Div. Polym. Chem. 1992, 33, 1233.
48. (b) Jiang, Z.; Dahlen, G. M.; Houseknecht, K.; Sen, A. Macromolecules 1992, 25, 2999.
49. For a recent review, see: Sen, A. Acc. Chem. Res. 1993, 26, 303.
50. A mechanism involving cationic Pd-carbene species has been proposed for the copolymerization of propylene with CO; see: Batistini, A.; Consiglio, G. Organometallics 1992, 11, 1766.
51. With regard to the alkyl to acyl reaction step (Scheme 1), recent studies have demonstrated that alkyl migration rather than carbonyl insertion is the preferred mechanism for cationic palladium complexes: van Leeuwen, P. W. N. M.; Roobeek, C. F.; van der Heijden, H. J. Am. Chem. Soc. 1994, 116, 12117.
52. (a) Sishta, C.; Hathorn, R. M.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 1112.
53. (b) Resconi, L.; Bossi, S.; Abis, L. Macromolecules 1990, 23, 4489.
54. (a) Jolly, C. A.; Marynick, D. S. J. Am. Chem. Soc. 1989, 111, 7968.
55. (b) Lauher, J. W.; Hoffmann, R. J. Am. Chem. Soc. 1976, 98, 1729.
56. Dahmen, K. H.; Hedden, D.; Burwell, R. L., Jr.; Marks, T. J. Langmuir 1988, 4, 1212.
57. Gassman, P. G.; Callstrom, M. R. J. Am. Chem. Soc. 1987,109, 7875.
58. n is carried out in MeCN solution.
59. 6 by the addition of the carboxylic acid to an Al-O bond is similar to the reaction during the formation of carboxylate alumoxanes from the aluminum oxides; see: Landry, C. C.; Pappé, N.; Mason, M. R.; Apblett, A. W.; Tyler, A. N.; MacInnes, A. N.; Barron, A. R. J. Mater. Chem. 1995, 5, 331.
60. Koide, Y.; Barron, A. R. Organometallics 1995, 14, 4026.
61. Sobota, P.; Mustafa, M. O.; Utko, J.; Lis, T. J. Chem. Soc., Dalton Trans. 1990, 1809.
62. 2 has been determined by X-ray crystallography: C-O = 1.254(4) and 1.259(5) Å, O-C-O = 122.7(3)°: Barron, A. R. Unpublished results.
63. Henderson, R. A. J. Chem. Soc., Dalton Trans. 1995, 177.
64. Dickerson, R. E.; Geis, I. Hemoglobin; Benjamin/Cummings: Menlo Park, CA, 1983.
65. Meyer, T. E.; Kamen, M. D. Adv. Protein Chem. 1982, 35, 105.
66. See for example: (a) Tang, S. C.; Koch, S.; Papaefthymiou, G. C.; Foner, S.; Frankel, R. B.; Ibers, J. A.; Holm, R. H. J. Am. Chem. Soc. 1976, 98, 2414. (b) Lane, R. W.; Ibers, J. A.; Frankel, R. B.; Papaefthymiou, G. C.; Holm, R. H. J. Am. Chem. Soc. 1977, 99, 84. (c) Collman, J. P. Acc. Chem. Res. 1977, 10, 265. Groves, J. T. Adv. Inorg. Biochem. 1979, 1, 119.
67. See for example: (a) Tang, S. C.; Koch, S.; Papaefthymiou, G. C.; Foner, S.; Frankel, R. B.; Ibers, J. A.; Holm, R. H. J. Am. Chem. Soc. 1976, 98, 2414. (b) Lane, R. W.; Ibers, J. A.; Frankel, R. B.; Papaefthymiou, G. C.; Holm, R. H. J. Am. Chem. Soc. 1977, 99, 84. (c) Collman, J. P. Acc. Chem. Res. 1977, 10, 265. Groves, J. T. Adv. Inorg. Biochem. 1979, 1, 119.
68. See for example: (a) Tang, S. C.; Koch, S.; Papaefthymiou, G. C.; Foner, S.; Frankel, R. B.; Ibers, J. A.; Holm, R. H. J. Am. Chem. Soc. 1976, 98, 2414. (b) Lane, R. W.; Ibers, J. A.; Frankel, R. B.; Papaefthymiou, G. C.; Holm, R. H. J. Am. Chem. Soc. 1977, 99, 84. (c) Collman, J. P. Acc. Chem. Res. 1977, 10, 265. Groves, J. T. Adv. Inorg. Biochem. 1979, 1, 119.
69. See for example: (a) Tang, S. C.; Koch, S.; Papaefthymiou, G. C.; Foner, S.; Frankel, R. B.; Ibers, J. A.; Holm, R. H. J. Am. Chem. Soc. 1976, 98, 2414. (b) Lane, R. W.; Ibers, J. A.; Frankel, R. B.; Papaefthymiou, G. C.; Holm, R. H. J. Am. Chem. Soc. 1977, 99, 84. (c) Collman, J. P. Acc. Chem. Res. 1977, 10, 265. Groves, J. T. Adv. Inorg. Biochem. 1979, 1, 119.
70. (e) Armstrong, W. H.; Spool, A.; Papaefthymiou, G. C.; Frankel, R. B.; Lippard, S. J. J. Am. Chem. Soc. 1984, 106, 3653.
71. (f) Spool, A.; Williams, I. D.; Lippard, S. J. Inorg. Chem. 1986, 24, 2156.
72. (g) Caradonna, J. P.; Reddy, P. R.; Holm, R. H. J. Am. Chem. Soc. 1988, 110, 2139.
73. (h) Craig, J. A.; Holm, R. H. J. Am. Chem. Soc. 1989, 111, 2111.
74. MolEN, An Interactive Structure Solution Program; Enraf-Nonius: Delft, The Netherlands, 1990.
75. International Tables for X-Ray Crystallography; Kynoch Press: Birmingham, U.K., 1974; Vol. 4.
76. Healy, M. D.; Wierda, D. A.; Barron, A. R. Organometallics 1988, 7, 2543.
77. Nicolet Instruments Corp., Madison, WI, 1988.