Bifunctional Lewis acids. Synthesis and olefin polymerization chemistry of the 1,1-Di[bis(perfluorophenyl)boryl]alkenes RCH=C[B(C6F5)2]2 (R = t-Bu, C6H5, C6F5)

Organometallics

Volumn 17, Issue 16, 1998, Pages 3557-3566

  Köhler, Katrin ^a   Piers, Warren E ^a   Jarvis, Adam P ^b   Xin, S ^b   Feng, Y ^b   Bravakis, A M ^b   Collins, Scott ^b   Clegg, William ^c   Yap, Glenn P A ^d   Marder, Todd B ^e  

^a UNIVERSITY OF CALGARY   (Canada)

^b UNIVERSITY OF WATERLOO   (Canada)

^c NEWCASTLE UNIVERSITY   (United Kingdom)

^d UNIVERSITY OF WINDSOR   (Canada)

^e DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000965943     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980259e     Document Type: Article

References (73)

1. For recent reviews see (a) Kaminsky, W.; Arndt, M. Adv. Polym. Sci. 1997, 127, 144. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (c) Brintzinger, H. H.; Fischer D.; Mülhaupt R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (c) Möhring, P. C.; Coville, N. J. J. Organomet. Chem. 1994, 479, 1.
2. For recent reviews see (a) Kaminsky, W.; Arndt, M. Adv. Polym. Sci. 1997, 127, 144. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (c) Brintzinger, H. H.; Fischer D.; Mülhaupt R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (c) Möhring, P. C.; Coville, N. J. J. Organomet. Chem. 1994, 479, 1.
3. For recent reviews see (a) Kaminsky, W.; Arndt, M. Adv. Polym. Sci. 1997, 127, 144. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (c) Brintzinger, H. H.; Fischer D.; Mülhaupt R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (c) Möhring, P. C.; Coville, N. J. J. Organomet. Chem. 1994, 479, 1.
4. For recent reviews see (a) Kaminsky, W.; Arndt, M. Adv. Polym. Sci. 1997, 127, 144. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (c) Brintzinger, H. H.; Fischer D.; Mülhaupt R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (c) Möhring, P. C.; Coville, N. J. J. Organomet. Chem. 1994, 479, 1.
5. (a) Deck, P. A.; Beswick, C. L.; Marks, T. J. J. Am Chem. Soc. 1998, 120, 1772.
6. (b) Chen, Y.-X.; Stern, C. L.; Marks T. J. J. Am. Chem. Soc. 1997 119, 2582.
7. (c) Chen, Y.-X.; Stern, C. L.; Yang, S.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 12451.
8. (d) Giardello M. A.; Eisen, M. S.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 12114.
9. (e) Hlatky, G. G.; Eckman, R. R.; Turner, H. W. Organometalics 1992, 11, 1413.
10. (f) Yang, X.; Stern, C. L.; Marks, T. J. Organometallics 1991, 10, 840.
11. (g) Hlatky, G. G.; Turner, H. W.; Eckman, R. R. J. Am. Chem. Soc. 1989, 111, 2728.
12. (a) For a recent review see: Reddy, S. S.; Sivaram, S. Prog. Polym. Sci. 1995, 20, 309.
13. See also: (b) Harlan, C. J.; Bott, S. G.; Barron, A. R. J. Am. Chem. Soc. 1995, 117, 6465. (c) Harlan, C. J.; Mason, M. R.; Barron, A. R. Organometallics 1994, 13, 2957. (d) Pasynkiewicz, S. Polyhedron 1990, 9, 429.
14. See also: (b) Harlan, C. J.; Bott, S. G.; Barron, A. R. J. Am. Chem. Soc. 1995, 117, 6465. (c) Harlan, C. J.; Mason, M. R.; Barron, A. R. Organometallics 1994, 13, 2957. (d) Pasynkiewicz, S. Polyhedron 1990, 9, 429.
15. See also: (b) Harlan, C. J.; Bott, S. G.; Barron, A. R. J. Am. Chem. Soc. 1995, 117, 6465. (c) Harlan, C. J.; Mason, M. R.; Barron, A. R. Organometallics 1994, 13, 2957. (d) Pasynkiewicz, S. Polyhedron 1990, 9, 429.
16. (a) Sishta, C.; Hathorn, R. M.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 1112.
17. (b) Gassman, P. G.; Callstrom, M. R. J. Am. Chem. Soc. 1987, 109, 7875.
18. (a) Bochmann, M.; Lancaster, S. J. Organometallics 1993, 12, 633.
19. (b) Bochmann, M.; Lancaster, S. J. J. Organomet. Chem. 1992, 434, C1.
20. (c) Chien, J. C. W.; Tsai, W.-M.; Rausch, M. D J. Am. Chem. Soc. 1991, 113, 8570.
21. (d) Turner, H. W. Eur. Pat. Appl. EP 0277004, 1988.
22. (a) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015.
23. (b) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1991, 113, 3623. For work on related boranes, see ref 2c.
24. Piers, W. E.; Chivers, T. Chem. Soc. Rev. 1997, 345.
25. For a review, see: Strauss, S. H. Chem. Rev. 1993, 93, 927.
26. (a) Jia, L.; Yang, X.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 842.
27. - to cationic methylzirconocene complexes, even in polar solvents (e.g., toluene:chlorobenzene mixtures) at low temperatures (i.e., Zr-Me signals coupled to F), although solvent-separated, ion-pairs predominate under these conditions. Xin, S.; Collins, S. manuscript in preparation.
28. - to cationic methylzirconocene complexes, even in polar solvents (e.g., toluene:chlorobenzene mixtures) at low temperatures (i.e., Zr-Me signals coupled to F), although solvent-separated, ion-pairs predominate under these conditions. Xin, S.; Collins, S. manuscript in preparation.
29. (a) Jia L.; Yang, X.; Stern, C.; Marks, T. J. Organometallics 1994, 13, 3755.
30. (b) Marks, T. J.; Jia, L.; Yang, X. U.S. Patent 5,447,895, 1995 (Northwestern University).
31. (c) Galsworthy, J. R.; Green, M. L. H.; Williams, V. C.; Chernega, A. N. Polyhedron 1998, 17, 119.
32. 9a
33. Parks, D. J.; Spence, R. E. v H.; Piers, W. E. Angew. Chem., Int. Ed. Engl. 1995, 34, 809.
34. 2 is highly reactive toward neutral bis-(alkyl)zirconocenes, see: (a) Spence, R. E. v H.; Parks, D. J.; Piers, W. E.; MacDonald, M.; Zaworotko, M. J.; Rettig, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1230. (b) Sun, Y.; Piers, W. E.; Rettig, S. J. Organometallics 1996, 15, 4110. (c) Sun, Y.; Spence R. E. v H.; Piers, W. E.; Parvez, M.; Yap, G. P. A. J. Am. Chem. Soc. 1997, 119, 5132. (d) Piers, W. E. Chem. Eur. J. 1998, 4, 13.
35. 2 is highly reactive toward neutral bis-(alkyl)zirconocenes, see: (a) Spence, R. E. v H.; Parks, D. J.; Piers, W. E.; MacDonald, M.; Zaworotko, M. J.; Rettig, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1230. (b) Sun, Y.; Piers, W. E.; Rettig, S. J. Organometallics 1996, 15, 4110. (c) Sun, Y.; Spence R. E. v H.; Piers, W. E.; Parvez, M.; Yap, G. P. A. J. Am. Chem. Soc. 1997, 119, 5132. (d) Piers, W. E. Chem. Eur. J. 1998, 4, 13.
36. 2 is highly reactive toward neutral bis-(alkyl)zirconocenes, see: (a) Spence, R. E. v H.; Parks, D. J.; Piers, W. E.; MacDonald, M.; Zaworotko, M. J.; Rettig, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1230. (b) Sun, Y.; Piers, W. E.; Rettig, S. J. Organometallics 1996, 15, 4110. (c) Sun, Y.; Spence R. E. v H.; Piers, W. E.; Parvez, M.; Yap, G. P. A. J. Am. Chem. Soc. 1997, 119, 5132. (d) Piers, W. E. Chem. Eur. J. 1998, 4, 13.
37. 2 is highly reactive toward neutral bis-(alkyl)zirconocenes, see: (a) Spence, R. E. v H.; Parks, D. J.; Piers, W. E.; MacDonald, M.; Zaworotko, M. J.; Rettig, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1230. (b) Sun, Y.; Piers, W. E.; Rettig, S. J. Organometallics 1996, 15, 4110. (c) Sun, Y.; Spence R. E. v H.; Piers, W. E.; Parvez, M.; Yap, G. P. A. J. Am. Chem. Soc. 1997, 119, 5132. (d) Piers, W. E. Chem. Eur. J. 1998, 4, 13.
38. An X-ray structural analysis of 2a established the connectivity and general features of the compound's structure; however, severe disorder precluded adequate refinement of the details associated with the structure.
39. For examples, see: (a) Wrackmeyer, B.; Nöth, H. Chem. Ber. 1977, 110, 1086. (b) Wrackmeyer, B. Z. Naturforsch. 1982, 376, 788. (c) Maderna, A.; Pritzkow, H.; Siebert, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 1501. (d) Schulz, H.; Gabbert, G.; Pritzkow, H.; Siebert, W. Chem. Ber. 1993, 126, 1593. (e) Curtis, M. A.; Müller, T.; Beez, V.; Pritzkow, H.; Siebert, W.; Grimes, R. N. Inorg. Chem. 1997, 36, 3602. (f) Wrackmeyer, B.; Schanz, H.-J.; Milius, W. Angew. Chem. 1997, 109, 1145. (g) Meller, A.; Maringgele, W.; Elter, G.; Bromm, D.; Noltemeyer, M.; Sheldrick, G. M. Chem. Ber. 1987, 120, 1437. (h) Köster, R.; Boese, R.; Wrackmeyer, B.; Schanz, H.-J. J. Chem. Soc., Chem. Commun. 1995, 1691.
40. For examples, see: (a) Wrackmeyer, B.; Nöth, H. Chem. Ber. 1977, 110, 1086. (b) Wrackmeyer, B. Z. Naturforsch. 1982, 376, 788. (c) Maderna, A.; Pritzkow, H.; Siebert, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 1501. (d) Schulz, H.; Gabbert, G.; Pritzkow, H.; Siebert, W. Chem. Ber. 1993, 126, 1593. (e) Curtis, M. A.; Müller, T.; Beez, V.; Pritzkow, H.; Siebert, W.; Grimes, R. N. Inorg. Chem. 1997, 36, 3602. (f) Wrackmeyer, B.; Schanz, H.-J.; Milius, W. Angew. Chem. 1997, 109, 1145. (g) Meller, A.; Maringgele, W.; Elter, G.; Bromm, D.; Noltemeyer, M.; Sheldrick, G. M. Chem. Ber. 1987, 120, 1437. (h) Köster, R.; Boese, R.; Wrackmeyer, B.; Schanz, H.-J. J. Chem. Soc., Chem. Commun. 1995, 1691.
41. For examples, see: (a) Wrackmeyer, B.; Nöth, H. Chem. Ber. 1977, 110, 1086. (b) Wrackmeyer, B. Z. Naturforsch. 1982, 376, 788. (c) Maderna, A.; Pritzkow, H.; Siebert, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 1501. (d) Schulz, H.; Gabbert, G.; Pritzkow, H.; Siebert, W. Chem. Ber. 1993, 126, 1593. (e) Curtis, M. A.; Müller, T.; Beez, V.; Pritzkow, H.; Siebert, W.; Grimes, R. N. Inorg. Chem. 1997, 36, 3602. (f) Wrackmeyer, B.; Schanz, H.-J.; Milius, W. Angew. Chem. 1997, 109, 1145. (g) Meller, A.; Maringgele, W.; Elter, G.; Bromm, D.; Noltemeyer, M.; Sheldrick, G. M. Chem. Ber. 1987, 120, 1437. (h) Köster, R.; Boese, R.; Wrackmeyer, B.; Schanz, H.-J. J. Chem. Soc., Chem. Commun. 1995, 1691.
42. For examples, see: (a) Wrackmeyer, B.; Nöth, H. Chem. Ber. 1977, 110, 1086. (b) Wrackmeyer, B. Z. Naturforsch. 1982, 376, 788. (c) Maderna, A.; Pritzkow, H.; Siebert, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 1501. (d) Schulz, H.; Gabbert, G.; Pritzkow, H.; Siebert, W. Chem. Ber. 1993, 126, 1593. (e) Curtis, M. A.; Müller, T.; Beez, V.; Pritzkow, H.; Siebert, W.; Grimes, R. N. Inorg. Chem. 1997, 36, 3602. (f) Wrackmeyer, B.; Schanz, H.-J.; Milius, W. Angew. Chem. 1997, 109, 1145. (g) Meller, A.; Maringgele, W.; Elter, G.; Bromm, D.; Noltemeyer, M.; Sheldrick, G. M. Chem. Ber. 1987, 120, 1437. (h) Köster, R.; Boese, R.; Wrackmeyer, B.; Schanz, H.-J. J. Chem. Soc., Chem. Commun. 1995, 1691.
43. For examples, see: (a) Wrackmeyer, B.; Nöth, H. Chem. Ber. 1977, 110, 1086. (b) Wrackmeyer, B. Z. Naturforsch. 1982, 376, 788. (c) Maderna, A.; Pritzkow, H.; Siebert, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 1501. (d) Schulz, H.; Gabbert, G.; Pritzkow, H.; Siebert, W. Chem. Ber. 1993, 126, 1593. (e) Curtis, M. A.; Müller, T.; Beez, V.; Pritzkow, H.; Siebert, W.; Grimes, R. N. Inorg. Chem. 1997, 36, 3602. (f) Wrackmeyer, B.; Schanz, H.-J.; Milius, W. Angew. Chem. 1997, 109, 1145. (g) Meller, A.; Maringgele, W.; Elter, G.; Bromm, D.; Noltemeyer, M.; Sheldrick, G. M. Chem. Ber. 1987, 120, 1437. (h) Köster, R.; Boese, R.; Wrackmeyer, B.; Schanz, H.-J. J. Chem. Soc., Chem. Commun. 1995, 1691.
44. For examples, see: (a) Wrackmeyer, B.; Nöth, H. Chem. Ber. 1977, 110, 1086. (b) Wrackmeyer, B. Z. Naturforsch. 1982, 376, 788. (c) Maderna, A.; Pritzkow, H.; Siebert, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 1501. (d) Schulz, H.; Gabbert, G.; Pritzkow, H.; Siebert, W. Chem. Ber. 1993, 126, 1593. (e) Curtis, M. A.; Müller, T.; Beez, V.; Pritzkow, H.; Siebert, W.; Grimes, R. N. Inorg. Chem. 1997, 36, 3602. (f) Wrackmeyer, B.; Schanz, H.-J.; Milius, W. Angew. Chem. 1997, 109, 1145. (g) Meller, A.; Maringgele, W.; Elter, G.; Bromm, D.; Noltemeyer, M.; Sheldrick, G. M. Chem. Ber. 1987, 120, 1437. (h) Köster, R.; Boese, R.; Wrackmeyer, B.; Schanz, H.-J. J. Chem. Soc., Chem. Commun. 1995, 1691.
45. For examples, see: (a) Wrackmeyer, B.; Nöth, H. Chem. Ber. 1977, 110, 1086. (b) Wrackmeyer, B. Z. Naturforsch. 1982, 376, 788. (c) Maderna, A.; Pritzkow, H.; Siebert, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 1501. (d) Schulz, H.; Gabbert, G.; Pritzkow, H.; Siebert, W. Chem. Ber. 1993, 126, 1593. (e) Curtis, M. A.; Müller, T.; Beez, V.; Pritzkow, H.; Siebert, W.; Grimes, R. N. Inorg. Chem. 1997, 36, 3602. (f) Wrackmeyer, B.; Schanz, H.-J.; Milius, W. Angew. Chem. 1997, 109, 1145. (g) Meller, A.; Maringgele, W.; Elter, G.; Bromm, D.; Noltemeyer, M.; Sheldrick, G. M. Chem. Ber. 1987, 120, 1437. (h) Köster, R.; Boese, R.; Wrackmeyer, B.; Schanz, H.-J. J. Chem. Soc., Chem. Commun. 1995, 1691.
46. For examples, see: (a) Wrackmeyer, B.; Nöth, H. Chem. Ber. 1977, 110, 1086. (b) Wrackmeyer, B. Z. Naturforsch. 1982, 376, 788. (c) Maderna, A.; Pritzkow, H.; Siebert, W. Angew. Chem., Int. Ed. Engl. 1996, 35, 1501. (d) Schulz, H.; Gabbert, G.; Pritzkow, H.; Siebert, W. Chem. Ber. 1993, 126, 1593. (e) Curtis, M. A.; Müller, T.; Beez, V.; Pritzkow, H.; Siebert, W.; Grimes, R. N. Inorg. Chem. 1997, 36, 3602. (f) Wrackmeyer, B.; Schanz, H.-J.; Milius, W. Angew. Chem. 1997, 109, 1145. (g) Meller, A.; Maringgele, W.; Elter, G.; Bromm, D.; Noltemeyer, M.; Sheldrick, G. M. Chem. Ber. 1987, 120, 1437. (h) Köster, R.; Boese, R.; Wrackmeyer, B.; Schanz, H.-J. J. Chem. Soc., Chem. Commun. 1995, 1691.
47. Leung, S.-W.; Singleton, D. A. J. Org. Chem. 1997, 62, 1955 and references therein.
48. Kidd, R. G. In NMR of Newly Accessible Nuclei; Laszlo, P., Ed.; Academic Press: New York, 1983; Vol. 2.
49. Gordon, A. J.; Ford, R. A. The Chemist's Companion; Wiley and Sons: New York, 1972; p 108.
50. Köhler, K.; Piers, W. E. Can. J. Chem., submitted for publication.
51. 2 and 1b had essentially the same outcome but were not studied in as much detail.
52. (a) Buchwald, S. L.; Watson, B. T.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 2544.
53. (b) Neilsen, R. B.; Buchwald, S. L. Chem. Rev. 1988, 88, 1047.
54. Chen, Y.-X.; Marks, T. J. Organometallics 1997, 16, 3649.
55. Horton, A. D.; de With, J. Organometallics 1997, 16, 5424.
56. Krishnamurthy, S.; Brown, H. C. J. Org. Chem. 1980, 45, 849.
57. (b) Yoshida, T.; Negishi, E. J. Chem. Soc., Chem. Commun. 1974, 763.
58. (c) Pelter A.; Smith, K.; Brown, H. C. Borane Reagents; Academic Press: New York, 1988; p 22-23.
59. 2. The precontacting time reflects the amount of time needed to fill the bomb in the glovebox followed by removal and attachment to the reactor system.
60. Bochmann, M.; Lancaster, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 1634.
61. Complex 4a reacts with 1 equiv of ethylene to form a compound of unknown structure: Köhler, K.; Piers, W. E. Unpublished results.
62. 2 are mixed at room temperature.
63. (a) Marques, M. M.; Tait, P. J. T.; Mejzlík, J.; Dias, A. R. J. Polym. Sci., Part A. 1998, 36, 573.
64. (b) Tait, P. J. T. In Transition Metal Catalyzed Polymerization: Alkenes and Dienes; Quirk, R. P., Ed.; Hartwood Acadademic Publishers: New York, 1983; p 115.
65. Shriver, D. F.; Drezdzon, M. A. The Manipulation of Air-Sensitive Compounds, 2nd ed.; Wiley: New York, 1986.
66. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518.
67. Wrackmeyer, B.; Kundler, S.; Boese, R. Chem. Ber. 1993, 126, 1361.
68. Samuel, E.; Rausch, M. D. J. Am. Chem. Soc. 1973, 95, 6263.
69. (a) Jordan, R. F.; Bajgur, C. S.; Dasher, W. E.; Rheingold, A. L. Organometallics 1987, 6, 1041.
70. (b) Gell, K. I.; Posin, B.; Schwartz, J.; Williams, G. M. J. Am. Chem. Soc. 1982, 104, 1846.
71. Chambers, R. D.; Chivers, T. J. Chem. Soc. 1965, 3933.
72. Biagini, P.; Lugli, G.; Garbassi, F.; Andreussi, P. Eur. Pat. Appl. EP 667,357, 1995.
73. Sheldrick, G. M. SHELXTL, version 5; Bruker AXS Inc.: Madison, WI, 1994.