rac-[Ethylenebis(2-(thexyldimethylsiloxy)indenyl)]zirconium dichloride: Synthesis, molecular structure and olefin polymerization catalysis

Journal of Organometallic Chemistry

Volumn 559, Issue 1-2, 1998, Pages 65-72

  Leino, Reko ^a   Luttikhedde, Hendrik J G ^a   Lehmus, Petri ^b   Wilén, Carl Eric ^a   Sjöholm, Rainer ^a   Lehtonen, Ari ^c   Seppälä, Jukka V ^b   Näsman, Jan H ^a,d  

^a ÅBO AKADEMI UNIVERSITY   (Finland)

^b AALTO UNIVERSITY   (Finland)

^c UNIVERSITY OF TURKU   (Finland)

^d GE Healthcare Bio Sciences AB   (Sweden)

Author keywords

ansa Metallocene; Indenyl; Olefin polymerization; Siloxy; Zirconium

Indexed keywords

GYMNOMYZA SAMOENSIS;

EID: 0002072193     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(98)00405-7     Document Type: Article

References (44)

1. For recent reviews, see: (a) P.C. Möhring, N.J. Coville, J. Organomet. Chem. 479 (1994) 1. (b) K.B. Sinclair, R.B. Wilson, Chem. Ind. 20 (1994) 257. (c) H.H. Brintzinger, D. Fischer, R. Mülhaupt, B. Rieger, R. Waymouth, Angew. Chem. Int. Ed. Engl. 34 (1995) 1143. (d) M. Bochmann, J. Chem. Soc. Dalton Trans. (1996) 255. (e) W. Kaminsky, M. Arndt, Adv. Polym. Sci. 127 (1997) 143.
2. For recent reviews, see: (a) P.C. Möhring, N.J. Coville, J. Organomet. Chem. 479 (1994) 1. (b) K.B. Sinclair, R.B. Wilson, Chem. Ind. 20 (1994) 257. (c) H.H. Brintzinger, D. Fischer, R. Mülhaupt, B. Rieger, R. Waymouth, Angew. Chem. Int. Ed. Engl. 34 (1995) 1143. (d) M. Bochmann, J. Chem. Soc. Dalton Trans. (1996) 255. (e) W. Kaminsky, M. Arndt, Adv. Polym. Sci. 127 (1997) 143.
3. For recent reviews, see: (a) P.C. Möhring, N.J. Coville, J. Organomet. Chem. 479 (1994) 1. (b) K.B. Sinclair, R.B. Wilson, Chem. Ind. 20 (1994) 257. (c) H.H. Brintzinger, D. Fischer, R. Mülhaupt, B. Rieger, R. Waymouth, Angew. Chem. Int. Ed. Engl. 34 (1995) 1143. (d) M. Bochmann, J. Chem. Soc. Dalton Trans. (1996) 255. (e) W. Kaminsky, M. Arndt, Adv. Polym. Sci. 127 (1997) 143.
4. For recent reviews, see: (a) P.C. Möhring, N.J. Coville, J. Organomet. Chem. 479 (1994) 1. (b) K.B. Sinclair, R.B. Wilson, Chem. Ind. 20 (1994) 257. (c) H.H. Brintzinger, D. Fischer, R. Mülhaupt, B. Rieger, R. Waymouth, Angew. Chem. Int. Ed. Engl. 34 (1995) 1143. (d) M. Bochmann, J. Chem. Soc. Dalton Trans. (1996) 255. (e) W. Kaminsky, M. Arndt, Adv. Polym. Sci. 127 (1997) 143.
5. For recent reviews, see: (a) P.C. Möhring, N.J. Coville, J. Organomet. Chem. 479 (1994) 1. (b) K.B. Sinclair, R.B. Wilson, Chem. Ind. 20 (1994) 257. (c) H.H. Brintzinger, D. Fischer, R. Mülhaupt, B. Rieger, R. Waymouth, Angew. Chem. Int. Ed. Engl. 34 (1995) 1143. (d) M. Bochmann, J. Chem. Soc. Dalton Trans. (1996) 255. (e) W. Kaminsky, M. Arndt, Adv. Polym. Sci. 127 (1997) 143.
6. (a) W. Spaleck, F. Küber, A. Winter, J. Rohrmann, B. Bachmann, M. Antberg, V. Dolle, E.F. Paulus, Organometallics 13 (1994) 954.
7. (b) W. Spaleck, M. Antberg, B. Aulbach, B. Bachmann, V. Dolle, S. Haftka, F. Küber, J. Rohrmann, A. Winter, in: G. Fink, R. Mülhaupt, H.H. Brintzinger (Eds.), Ziegler Catalysts, Springer, Berlin, 1995, p. 83.
8. (c) U. Stehling, J. Diebold, R. Kirsten, W. Roll, H.H. Brintzinger, S. Jüngling, R. Mülhaupt, F. Langhauser, Organometallics 13 (1994) 964.
9. (d) S. Jüngling, R. Mülhaupt, U. Stehling, H.H. Brintzinger, D. Fischer, F. Langhauser, J. Polym. Sci., Part A: Polym. Chem. 33 (1995) 1305.
10. (a) R. Leino, H. Luttikhedde, C.-E. Wilén, R. Sillanpää, J.H. Näsman, Organometallics 15 (1996) 2450.
11. (b) R. Leino, H.J.G. Luttikhedde, P. Lehmus, C.-E. Wilén, R. Sjöholm, A. Lehtonen, J.V. Seppälä, J.H. Näsman, Macromolecules 30 (1997) 3477.
12. (c) R. Leino, H.J.G. Luttikhedde, C.-E. Wilén, J.H. Näsman, Polym. Mater. Sci. Eng. 76 (1997) 328.
13. (d) R. Leino, H. Luttikhedde, C.-E. Wilén, J.H. Näsman, Int. Pat. Appl. PCT/FI97/ 00049.
14. m = 149 vs 148°C).
15. The 1-substituted analogue of 1 is aspecific but polymerizes ethylene with high activity. A detailed description will be given in a subsequent paper. For synthesis of the 1-substituted complexes, see: (a) R. Leino, H. Luttikhedde, A. Lehtonen, P. Ekholm, J.H. Näsman, J. Organomet. Chem 558 (1998) 179. (b) H.J.G. Luttikhedde, R. Leino, A. Lehtonen, J.H. Näsman, J. Organomet. Chem. 555 (1998) 127.
16. The 1-substituted analogue of 1 is aspecific but polymerizes ethylene with high activity. A detailed description will be given in a subsequent paper. For synthesis of the 1-substituted complexes, see: (a) R. Leino, H. Luttikhedde, A. Lehtonen, P. Ekholm, J.H. Näsman, J. Organomet. Chem 558 (1998) 179. (b) H.J.G. Luttikhedde, R. Leino, A. Lehtonen, J.H. Näsman, J. Organomet. Chem. 555 (1998) 127.
17. T.W. Greene, P.G.M. Wuts, Protective Groups in Organic Synthesis, 2nd ed., Wiley, New York, 1991, pp. 413-416.
18. 2SiCl in DBU/benzene. The stability of the former towards BuLi appears to be limited. All attempts to prepare the unbridged or bridged metallocene derivatives of the latter failed.
19. H.J.G. Luttikhedde, R.P. Leino, C.-E. Wilén, J.H. Näsman, M.J. Ahlgrén, T.A. Pakkanen, Organometallics 15 (1996) 3092.
20. F. Piemontesi, I. Camurati, L. Resconi, D. Balboni, A. Sironi, M. Moret, R. Zeigler, N. Piccolrovazzi, Organometallics 14 (1995) 1256.
21. E. Barsties, S. Schaible, M.-H. Prosenc, U. Rief, W. Roll, O. Weyand, B. Dorer, H.H. Brintzinger, J. Organomet. Chem. 520 (1996) 63.
22. W.A. Herrmann, J. Rohrmann, E. Herdtweck, W. Spaleck, A. Winter, Angew. Chem. Int. Ed. Engl. 28 (1989) 1511.
23. (a) A. Schäfer, E. Karl, L. Zsolnai, G. Huttner, H.H. Brintzinger, J. Organomet. Chem. 328 (1987) 87.
24. (b) H.H. Brintzinger, in: W. Kaminsky, H. Sinn (Eds.), Transition Metals and Organometallics as Catalysts for Olefin Polymerization, Springer, Berlin, 1988, p. 249.
25. G.M. Diamond, R.F. Jordan, J.L. Petersen, Organometallics 15 (1996) 4030.
26. p in order to maintain an approximately constant monomer concentration in the polymerization medium, see: (a) B. Rieger, X. Mu, D.T. Mallin, M.D. Rausch, J.C.W. Chien, Macromolecules 23 (1990) 3559; and (b) Ref. ([2]b). The ethylene polymerizations were carried out in a slightly different polymerization system and the activities are not directly comparable to those of the propylene polymerizations.
27. (a) J.C.W. Chien, R. Sugimoto, J. Polym. Sci., Part A: Polym. Chem. 29 (1991) 459.
28. (b) G.H. Llinas, R.O. Day, M.D. Rausch, J.C.W. Chien, Organometallics 12 (1993) 1283.
29. (c) C. Janiak, U. Versteeg, K.C.H. Lange, Weimann, E. Hahn, J. Organomet. Chem. 501 (1995) 219.
30. D.E. Richardson, N.G. Alameddin, M.F. Ryan, T.H. Hayes, J.R. Eyler, A.L. Siedle, J. Am. Chem. Soc. 118 (1996) 11244.
31. W. Spaleck, M. Antberg, J. Rohrmann, A. Winter, B. Bachmann, P. Kiprof, J. Behm, W.A. Herrmann, Angew. Chem. Int. Ed. Engl. 31 (1992) 1347.
32. (a) W. Kaminsky, O. Rabe, A.-M. Schauwienold, G.U. Schupfner, J. Hanss, J. Kopf, J. Organomet. Chem. 497 (1995) 181.
33. (b) L. Resconi, F. Piemontesi, I. Camurati, D. Balboni, A. Sironi, M. Moret, H. Rychlicki, R. Zeigler, Organometallics 15 (1996) 5046.
34. A. Razavi, L. Peters, L. Nafpliotis, J. Mol. Catal. A: Chem. 115 (1997) 129, and references therein.
35. R. Kravchenko, A. Masood, R.M. Waymouth, Organometallics 16 (1997) 3635.
36. See, for example: (a) V.V. Vickroy, H. Schneider, R.F. Abbott, J. Appl. Polym. Sci. 50 (1993) 551. (b) J.B.P. Soares, J.D. Kim, G.L. Rempel, Ind. Eng. Chem. Res. 36 (1997) 1144.
37. See, for example: (a) V.V. Vickroy, H. Schneider, R.F. Abbott, J. Appl. Polym. Sci. 50 (1993) 551. (b) J.B.P. Soares, J.D. Kim, G.L. Rempel, Ind. Eng. Chem. Res. 36 (1997) 1144.
38. calc,i and y being the experimental, calculated and average y values, respectively.
39. (a) W. Röll, H.H. Brintzinger, B. Rieger, R. Zolk, Angew. Chem. Int. Ed. Engl. 29 (1990) 279.
40. (b) K. Mashima, A. Nakamura, J. Organomet. Chem. 428 (1992) 49.
41. (c) C. Janiak, J. Organomet. Chem. 452 (1993) 63.
42. (d) R.H. Grubbs, G.W. Coates, Acc. Chem. Res. 29 (1996) 85.
43. TEXSAN-TEXRAY Structure Analysis Package, Version 5.0, Molecular Structure Corporation, Houston, TX, 1989.
44. C.K. Johnson, ORTEPII, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, TN, 1976.