Polymerization of α-Olefins and Butadiene and Catalytic Cyclotrimerization of 1-Alkynes by a New Class of Group IV Catalysts. Control of Molecular Weight and Polymer Microstructure via Ligand Tuning in Sterically Hindered Chelating Phenoxide Titanium and Zirconium Species

Journal of the American Chemical Society

Volumn 117, Issue 11, 1995, Pages 3008-3021

  van der Linden, Arjan ^a   Schaverien, Colin J ^a   Meijboom, Nico ^a   Ganter, Christian ^b   Orpen, A Guy ^b  

^a SHELL RESEARCH AND TECHNOLOGY CENTRE   (Netherlands)

^b UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001280507     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00116a006     Document Type: Article

References (101)

1. Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325.
2. Marks, T. J. Acc. Chem. Res. 1992, 25, 57.
3. Ewen, J. A. J. Am. Chem. Soc. 1984, 106, 6355.
4. Kaminsky, W.; Kiilper, K.; Brintzinger, H. H.; Wild, F. R. W. P. Angew. Chem. 1985, 97, 507.
5. Kaminsky, W. Angew. Makromol. Chem. 1986, 145, 149.
6. Hlatky, G. G.; Turner, H. W.; Eckman, R. R. J. Am. Chem. Soc. 1989, 111, 2728.
7. Jordan, R. F.; Dasher, W. E.; Echols, S. F. J. Am. Chem. Soc. 1986, 108, 1718.
8. Sinn, H.; Kaminsky, W. Adv. Organomet. Chem. 1980, 18, 99.
9. Resconi, L.; Piemontesi, F.; Franciscono, G.; Abis, L.; Fiorani, T. J. Am. Chem. Soc. 1992, 114, 1025.
10. Yang, X.; Stern, C. L.; Marks, T. J. Organometallics 1991, 10, 840.
11. Horton, A. D. Trends Polym. Sci. 1994, 2, 158. This is a useful and insightful review of α-olefin polymerization by metallocene catalysts.
12. Ewen, J. A.; Jones, R. L.; Ravazi, A.; Ferrara, J. D. J. Am. Chem. Soc. 1988, 110, 6255.
13. Farina, M.; Di Silvestra, G.; Sozzani, P. Prog. Polym. Sci. 1991, 16, 219. Llinas, G. H.; Day, R. O.; Rausch, M. D.; Chien, J. C. W. Organometallics 1993, 12, 1283.
14. Llinas, G. H.; Dong, S.-H.; Mallin, D. T.; Rausch, M. D.; Lin, Y.-G.; Winter, H. H.; Chien, J. C. W. Macromolecules 1992, 25, 1242. Babu, G. N.; Newmark, R. A.; Cheng, H. N.; Llinas, G. H.; Chien, J. C. W. Macromolecules 1992, 25, 7400.
15. Spaleck, W.; Küber, F.; Winter, A.; Rohrmann, J.; Bachmann, B.; Antberg, M.; Dolle, V.; Paulus, E. F. Organometallics 1994, 13, 954.
16. 2 (M = Ti, Zr, Hf)/MAO catalysts for olefin (co)polymerization. See: (a) Canich, J. M. European Patent 420436, 1991.(a) Canich, J. M. European Patent 420436, 1991.
17. Canich, J. M.; Hlatky, G. G.; Turner, H. W. U.S. Patent 542236, 1990.
18. Stevens, J. C.; Timmers, F. J.; Wilson, D. R.; Schmidt, G. F.; Nickias, P. N.; Rosen, R. K.; Knight, G. W.; Lai, S. European Patent 416815, 1990.
19. Campbell, R. E., Jr. U.S. Patent 5066741, 1991.
20. LaPointe, R. E. European Patent 468651, 1991.
21. LaPointe, R. E.; Rosen, R. K.; Nickias, P. N. European Patent 495 375, 1992.
22. W= ca. 2000, 60-90% r diads). Turner, H. W.; Hlatky, G. G.; Canich, J. M. PCT Int. Appl. WO 93/19103 filing date March 16, 1992.
23. 2 is reported to polymerize propene to isotactic polypropene Canich, J. M. U.S. 5026798.
24. 2/MAO has been claimed to polymerize propene to i-PP (90%m diads). Canich, J. M.; Turner, H. W. PCT Int. Appl. WO 92/12612 filing date December 26, 1991.
25. 2: Fandos, R.; Meetsma, A.; Teuben, J. H. Organometallics 1991, 10, 59.
26. 2}TiCl2: Fandos, R.; Teuben, J. H.; Helgesson, G.; Jagner, S. Organometallics 1991, 10, 1637.
27. 2: Hughes, A. K.; Meetsma, A.; Teuben, J. H. Organometallics 1993, 12, 1936 and refs 2–12 therein.
28. 5)(COT)ZrR: Sinnema, P.-J.; Meetsma, A,; Teuben, J. H. Organometallics 1993, 12, 184.
29. +: Uhrhammer, R.; Black, D. G.; Gardner, T. G.; Olsen, J. D.; Jordan, R. F. J. Am. Chem. Soc. 1993, 115, 8493.
30. Floriani, C.; Ciurli, S.; Chiesi-Villa, A.; Guastini, C. Angew. Chem., Int. Ed. Engl. 1987, 26, 70.
31. 2: Brand, H.; Arnold, J. J. Am. Chem. Soc. 1992, 114, 2266.
32. 2: Hessen, B.; Spek, A. L.; Teuben, J. H. Angew. Chem., Int. Ed. Engl. 1988, 27, 1058.
33. 2: Rieger, B. J. Organomet. Chem. 1991, 420, C17.
34. In lanthanide chemistry: (a) Schaverien, C. J. Advances in Organometallic Chemistry; Academic Press: New York, 1994; Vol. 36, p 283.
35. (OEP)MR (M = Y, Lu): Schaverien, C. J.; Orpen, A. G. Inorg. Chem. 1991, 30, 4968.
36. 2}2YR: Duchateau, R.; Van Wee, C. T.; Meetsma, A.; Teuben, J. H. J. Am. Chem. Soc. 1993, 115, 4931.
37. -: Bazan, G. C.; Schaefer, W. P.; Bercaw, J. E. Organometallics 1993, 12, 2126. See also reference 13.
38. Heppert, J. A.; Dietz, S. D.; Boyle, T. J.; Takusagawa, F. J. Am. Chem. Soc. 1989, 111, 1503.
39. Boyle, T. J.; Barnes, D. L.; Heppert, J. A.; Morales, L.; Takusagawa, F.; Connolly, J. W. Organometallics 1992, 11, 1112. Boyle, T. J.; Eilerts, N. W.; Heppert, J. A.; Takusagawa, F. Organometallics 1994, 13, 2218.
40. McConville, D. H.; Wolf, J. R.; Schrock, R. R. J. Am. Chem. Soc. 1993, 115, 4413.
41. 11 afforded a dimeric bisdiolate of unknown stoichiometry. Kruger, C.; Mynott, R.; Siedenbiedel, C.; Stehling, L.; Wilke, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 1668.
42. Miyatake, T.; Mizunuma, K.; Seki, Y.; Kakugo, M. Makromol. Chem., Rapid Commun. 1989, 10, 349.
43. Kakugo, M.; Miyatake, T.; Mizunuma, K.; Yagi, Y. Sumitomo Chemical Co. U.S. 5043, 408.
44. 9a,c
45. 4 as cocatalysts was recently filed (February 19, 1992). Mitsui Toatsu Chem. Inc. JP 05230133-A.
46. Chem. Express 1987, 2, 445.
47. Schaverien, C. J. Organometallics 1994, 13, 69.
48. Schaverien, C. J.; Meijboom, N.; Orpen, A. G. J. Chem. Soc., Chem. Commun, 1992, 124.
49. Schaverien, C. J.; Van der Linden, A. J.; Orpen, A. G. Polymer Preprints 1994, 35, 672. Abstract of Papers, 212th National Meeting of the American Chemical Society, San Diego, Spring 1994; American Chemical Society, Washington, DC, 1994; Abstract no. POLY 258. Schaverien, C. J.; Van der Linden, A. J. European Patent Appl. 606125 A2 priority date January 8, 1993.
50. Schrock, R. R.; Wengrovius, J. H. J. Organomet. Chem. 1981, 205, 319. Zucchini, U.; Albizzati, E.; Giannini, U. J. Organomet. Chem. 1971, 26, 357.
51. 2-catalyzed oxidative coupling of the 2,4-disubstituted phenol in MeOH (see the supplementary material). Capdvielle, P.; Maumy, M. Tetrahedron Lett. 1983, 24, 5611. Hewitt, D. G. J. Chem. Soc., C 1971, 1750. Kushioka, K. J. Org. Chem. 1983, 48, 4948.
52. Lingenfelter, D. S.; Helgeson, R. C.; Cram, D. J. J. Org. Chem. 1981, 46, 393.
53. Maruoka, K.; Itoh, T.; Araki, Y.; Shirasaka, T.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1988, 61, 2975.
54. Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310.
55. Miyashita, A.; Yasuda, A.; Tanaka, H.; Toniimi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932.
56. 2 is described in the supplementary material on a 10 g scale. This is based upon, or is a modification of, literature procedures.(a) Schaefer, J. R.; Higgins, J. J. Org. Chem. 1967, 32, 1607. (a) Schaefer, J. R.; Higgins, J. J. Org. Chem. 1967, 32, 1607.
57. Newman, M. S.; Karnes, H. A. J. Org. Chem. 1966, 31, 3980.
58. Snieckus, V.; Beaulieu, F. Synthesis 1992, 113.
59. Di Furia, F. Bull. Soc. Chim. Fr. 1991, 127, 734.
60. Figuly, G. D.; Loop, C. K.; Martin, J. C. J. Am. Chem. Soc. 1989, 111, 654. Block, E.; Eswarakrishnan, V.; Gemon, M.; Ofori-Okai, C. S.; Tang, K.; Zubieta, J. J. Am. Chem. Soc. 1989, 111, 658. Smith, K.; Lindsay, C. M.; Pritchard, G. J. J. Am. Chem. Soc. 1989, 111. 665.
61. 26d have also been synthesized and characterized by X-ray diffraction.
62. Corazza, F.; Floriani, C.; ChiesiVilla, A.; Guastini, C. Inorg. Chem. 1991, 30, 145.
63. Mazzanti, M.; Floriani, C.; Chiesi-Villa, A.; Guastini, C. J. Chem. Soc., Dalton Trans. 1989, 1793.
64. Toscano, P. J.; Schermerhorn, E. J.; Dettelbacher, C.; Macherone, D.; Zubieta, J. J. Chem. Soc., Chem. Commun. 1991, 933.
65. Jordan, R. F.; LaPointe, R. E.; Bajgur, C. S.; Echols, S. F.; Willett, R. J. Am. Chem. Soc. 1987, 109, 4111.
66. Bochmann, M.; Lancaster, S. J. Organometallics 1993, 12, 633.
67. Mintz, E. A.; Moloy, K. G.; Marks, T. J.; Day, V. W. J. Am. Chem. Soc. 1982, 104, 4692. Wolczanski, P. T.; Bercaw, J. E. Organometallics 1982, 1, 793.
68. Lee, I.-K.; Gauthier, W. J.; Ball, J. M.; Iyengar, B.; Collins, S. Organometallics 1992, 11, 2115.
69. Kaminsky, W.; Steiger, R. Polyhedron 1988, 7, 2375.
70. Llinas, G. H.; Day, R. O.; Rausch, M. D.; Chien, J. C. W. Organometallics 1993, 12, 1283. See also ref 32 for ethylene polymerization activities of Cp2ZrR2/MAO.
71. 2Co]. Hlatky, G. G.; Eckman, R. R.; Turner, H. W. Organometallics 1992, 11, 1413.
72. 3 is largely removed under vacuum from the commercially available MAO in toluene solution) dissolved in toluene. No notable cocatalystrelated differences in polymerization behavior were observed. See: Resconi, L.; Bossi, S.; Abis, L. Macromolecules 1990, 23, 4489.
73. e polyhexene are also reported in the literature,(a) Babu, G. N.; Newmark, R. A.; Chien, J. C. W. Macromolecules 1994, 27, 3383.
74. Asakura, T.; Demura, M.; Nishiyama, Y. Macromolecules 1991, 24, 2334.
75. Coughlin, E. B.; Bercaw, J. E. J. Am. Chem. Soc. 1992, 114, 7606.
76. Asanuma, T.; Nishimori, Y.; Ito, M.; Uchikawa, N.; Shiomura, T. Polym. Bull. 1991, 25, 567.
77. 13C NMR chemical shifts of various isotactic and syndiotactic poly(α-olefins). See also: (e) Asanuma, A.; Shiomura, T.; Nishimura, Y.; Uchikawa, N. Mitsui Chem. Co. European Pat. Appl. 403866.
78. Resconi, L.; Piemontesi, F.; Franciscono, G.; Abis, L.; Fiorani, T. J. Am. Chem. Soc. 1992, 114, 1025.
79. Liu, H. Q.; Deffieux, A.; Sigwalt, P. Makromol. Chem. 1991, 192, 2111.
80. Liu, H. Q.; Deffieux, A.; Sigwalt, P. Makromol. Chem. 1991, 192, 2125.
81. Foulds, G. A.; Bennet, A. M. A.; Nivan, M. L.; Thornton, D. A.; Cavell, K. J.; Desjardins, S.; Peacock, E. J. J. Mol. Catal. 1994, 87, 117.
82. 2Zr(H)Cl reacts with 4-octene to give the thermodynamically most stable Zr-n-octyl product.
83. Cooper, W. Polydienes by Coordination Catalysis in The Stereo Rubbers; Saltman, W. M., Ed.; Wiley: New York, 1977; pp 21-75.
84. Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539. McAlister, D. R.; Bercaw, J. E.; Bergman, R. G. J. Am. Chem. Soc. 1977, 99, 1666.
85. tBu gave the α.α'-disubstituted tantalacyclopentadiene as the kinetically favored product, which rearranged to the α,β' isomer as the thermodynamically favored product.
86. Assuming nonregioselective acetylene insertion into β, β'-ZrCP, this would yield a mixture of 1,2,4- and 1,2,3-trisubstituted benzenes. Presumably, the latter is not observed due to unfavorable sterics. Similarly, an α,β'-ZrCP would give 1,3,5- and 1,2,4-trisubstituted benzenes and α,α'-ZrCP 1,2,4-trisubstituted benzenes.
87. 2: Lang, H.; Herres, M.; Zsolnai, L.; Imhof, W. J. Organomet. Chem. 1991, 409, C7.
88. Stucky, G. D.; Sekutowsky, D. G. J. Am. Chem. Soc. 1976, 98, 1376. Teuben, J. H. Personal communication.
89. nph, see: Armitrage, J. B.; Entwistle, N.; Jones, E. R. H.; Whiting, M. C. J. Chem. Soc. 1954, 147.
90. Wielstra, Y.; Gambarotta, S.; Meetsma, A.; De Boer, J. L. Organometallics 1989, 8, 2696.
91. Pellecchia, C.; Grassi, A.; Immirzi, A. J. Am. Chem. Soc. 1993, 115, 1160.
92. Pellecchia, C.; Immirzi, A.; Grassi, A.; Zambellli, A. Organometallics 1993, 12, 4473.
93. Schaverien, C. J. Organometallics 1992, 11, 3476.
94. Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1991, 113, 3623.
95. Jordan, R. F. J. Chem. Educ. 1988, 65, 285.
96. Bochmann, M.; Kargar, G.; Jaggar, A. J. J. Chem. Soc., Chem. Commun. 1990, 1038.
97. Horton, A. D.; Frijns, J. H. G. Angew. Chem., Int. Ed. Engl. 1991, 30, 1152.
98. Santee, E. R., Jr.; Chang, R.; Morton, M. Polym. Lett. Ed. 1973, 11, 449.
99. Sheldrick, G. M. SHELXTL-PLUS Rev. 4.2, Gottingen, Germany, 1990.
100. SHELXL93: Sheldrick, G. M. J. Appl. Crystallogr. In Preparation.
101. International Tables for Crystallography, Vol. C; Kluwer: Doredrecht, 1992. International Tables for X-ray Crystallography, Vol. IV; Kynoch Press: Birmingham, 1974.