The First Fluorenyl ansa-Yttrocene Complexes: Synthesis, Structures, and Polymerization of Methyl Methacrylate

Organometallics

Volumn 18, Issue 24, 1999, Pages 5124-5129

  Lee, Min Hyung ^a   Hwang, Jeong Wook ^a   Kim, Youngjo ^a   Kim, Jindong ^a   Han, Yonggyu ^a   Do, Youngkyu ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001143673     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990471y     Document Type: Article

References (83)

1. For recent reviews of Group 4 metallocene and organolanthanide chemistry, see: (a) Kaminsky, W.; Arndt, M. Adv. Polym. Sci. 1997, 27, 144. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (c) Brintzinger, H. H.; Fisher, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (d) Edelmann, F. T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2466. (e) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865.
2. For recent reviews of Group 4 metallocene and organolanthanide chemistry, see: (a) Kaminsky, W.; Arndt, M. Adv. Polym. Sci. 1997, 27, 144. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (c) Brintzinger, H. H.; Fisher, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (d) Edelmann, F. T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2466. (e) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865.
3. For recent reviews of Group 4 metallocene and organolanthanide chemistry, see: (a) Kaminsky, W.; Arndt, M. Adv. Polym. Sci. 1997, 27, 144. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (c) Brintzinger, H. H.; Fisher, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (d) Edelmann, F. T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2466. (e) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865.
4. For recent reviews of Group 4 metallocene and organolanthanide chemistry, see: (a) Kaminsky, W.; Arndt, M. Adv. Polym. Sci. 1997, 27, 144. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (c) Brintzinger, H. H.; Fisher, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (d) Edelmann, F. T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2466. (e) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865.
5. For recent reviews of Group 4 metallocene and organolanthanide chemistry, see: (a) Kaminsky, W.; Arndt, M. Adv. Polym. Sci. 1997, 27, 144. (b) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (c) Brintzinger, H. H.; Fisher, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (d) Edelmann, F. T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2466. (e) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865.
6. (a) Ihara, E.; Nodono, M.; Katsura, K.; Adachi, Y.; Yasuda, H.; Yamagashira, M.; Hashimoto, H.; Kanehisa, N.; Kai, Y. Organometallics 1998, 17, 3945.
7. (b) Evans, W. J.; Forrestal, K J.; Ziller, J. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 774.
8. (c) Mitchell, J. P.; Hajela, S.; Brookhart, S. K.; Hardcastle, K. I.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 1045.
9. (d) Shapiro, P. J.; Cotter, W. D.; Schaefer, W. P.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1994, 116, 4623.
10. (a) Knjazhanski, S. Y.; Elizalde, L.; Cadenas, G.; Bulychev, B. M. J. Organomet. Chem. 1998, 568, 33.
11. (b) Mao, L.; Shén, Q. J. Polym. Sci., Part A: Polym. Chem. 1998, 36, 1593.
12. (c) Hultzsch, K. C.; Spaniol, T. P.; Okuda, J. Organometallics 1997, 16, 4845.
13. (d) Yasuda, H.; Tamai, H. Prog. Polym. Sci. 1993, 18, 1097.
14. (e) Yasuda, H.; Yamamoto, H.; Yamashita, M.; Yokota, K.; Nakamura, A.; Miyake, S.; Kai, Y.; Kanehisa, N. Macromolecules 1993, 26, 7134.
15. (f) Yasuda, H.; Yamamoto, H.; Yokota, K.; Miyake, S.; Nakamura, A. J. Am. Chem. Soc. 1992, 114, 4908.
16. (g) Yasuda, H.; Furo, M.; Yamamoto, H. Macromolecules 1992, 25, 5115.
17. For highly isotactic poly(methyl methacrylate) obtained by chiral lanthanidocenes, see: Giardello, M. A.; Yamamoto, Y.; Brard, L.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 3276.
18. (a) Arredondo, V. M.; McDonald, F. E.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 4871.
19. (b) Kretschmer, W. P.; Troyanov, S. I.; Meetsma, A.; Hessen, B.; Teuben, J. H. Organometallics 1998, 17, 284.
20. (c) Obora, Y.; Ohta, T.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1997, 119, 3745.
21. (d) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1998, 118, 9295.
22. (e) Haar, C. M.; Stern, C. L.; Marks, T. J. Organometallics 1996, 15, 1765.
23. (f) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157.
24. (g) Giardello, M. A.; Conticello, V. P.; Brard, L.; Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10241.
25. Akhnoukh, T.; Müller, J.; Qiao, K.; Li, X. F.; Fischer, R. D. J. Organomet. Chem. 1991, 408, 47.
26. (a) Rogers, R. D.; vann Bynum, R.; Atwood, J. L. J. Organomet. Chem. 1980, 192, 65.
27. (b) Ni, C.; Zhang, Z.; Deng, D.; Qian, C. J. Organomet. Chem. 1986, 306, 209.
28. (a) Evans, W. J.; Cano, D. A.; Greci, M. A.; Ziller, J. W. Organometallics 1999, 18, 1381.
29. (b) Roesky, P. W.; Denninger, U.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4486.
30. (c) Heeres, H. J.; Meetsma, A.; Teuben, J. H.; Rogers, R. D. Organometallics 1989, 8, 2637.
31. (d) Evans, W. J.; Chamberlain, L. R.; Ulibarri, T. A.; Ziller, J. W. J. Am. Chem. Soc. 1988, 110, 6423.
32. (e) Heeres, H. J.; Renkema, J.; Booij, M.; Meetsma, A.; Teuben, J. H. Organometallics 1988, 7, 2495.
33. (f) Rausch, M. D.; Morlarty, K. J.; Atwood, J. L.; Weeks, J. A.; Hunter, W. E.; Brittain, H. G. Organometallics 1986, 5, 1281.
34. (g) Evans, W. J.; Grate, J. W.; Choi, H. W.; Bloom, I.; Hunter, W. E.; Atwood, J. L. J. Am. Chem. Soc. 1985, 107, 941.
35. (h) Jeske, G.; Lauke, H.; Mauermann, H.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8091.
36. Jeske, G.; Schock, L. E.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1986, 107, 8103.
37. (a) Evans, W. J.; Olofson, J. M.; Zhang, H.; Atwood, J. L. Organometallics 1988, 7, 629.
38. (b) Schumann, H.; Albrecht, I.; Loebel, J.; Hahn, E.; Hossain, M. B.; van der Helm, D. Organometallics 1986, 5,1296.
39. Watson, P. L.; Whitney, J. F.; Harlow, R. L. Inorg. Chem. 1981, 20, 3271.
40. Tsutsui, M.; Chen, L.-B.; Bergbreiter, D. E.; Miyamoto, T. K. J. Am. Chem. Soc. 1982, 104, 855.
41. 2 symmetry, see: Herrmann, W. A.; Eppinger, J.; Spiegler, M.; Runte, O.; Anwander, R. Organometallics 1997, 16, 1813.
42. 4 symmetry, see: Stern, D.; Sabat, M.; Marks, T. J. J. Am. Chem. Soc. 1990, 112, 9558.
43. 1 symmetry, see: Giardello, M. A.; Conticello, V. P.; Brard, L.; Sabat, M.; Rheingold, A. L.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10212.
44. (a) Lee, M. H.; Park, J.-W.; Hong, C. S.; Woo, S. I.; Do, Y. J. Organomet. Chem. 1998, 561, 37.
45. (b) Razavi, A.; Peters, L.; Nafpliotis, L. J. Mol. Catal. A: Chem. 1997, 115, 129.
46. (c) Resconi, L.; Jones, R. L.; Rheingold, A. L.; Yap, G. P. L. Organometallics 1996, 15, 998
47. (d) Ewen, J. A.; Elder, M. J. In Ziegler Catalysts; Fink. G., Mülhaupt, R., Brintzinger, H. H., Eds.; Springer-Verlag: Berlin, Heidelberg, 1995; p 99.
48. (e) Razavi, A.; Vereeke, D.; Peters, L.; Dauw, K. D.; Nafpliotis, L.; Atwood, J. L. In Ziegler Catalysts; Fink. G., Mülhaupt, R., Brintzinger, H. H., Eds.; Springer-Verlag: Berlin, Heidelberg, 1995; p 111.
49. (f) Rieger, B.; Jany, G.; Fawzi, R.; Steimann, M. Organometallics 1994, 13, 647.
50. (g) Ewen, J. A.; Jones, R. L.; Razavi, A.; Ferrara, J. D. J. Am. Chem. Soc. 1988, 110, 6255.
51. Evans, W. J.; Gummersheimer, T. S.; Boyle, T. J.; Ziller, J. W. Organometallics 1994, 13, 1281.
52. (a) Sharma, R. K.; Sharma, C. P. J. Indian Chem. Soc. 1987, 64, 506.
53. (b) Sigalov, A. B.; Rybakova, L. F.; Syutkina, O. P.; Shifrina, R. R.; Bogachev, Yu. S.; Zhuravleva, I. L.; Beletskaya, I. P. Izv. Akad. Nauk SSSR, Ser. Khim. 1983, 918; Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1983, 833.
54. (b) Sigalov, A. B.; Rybakova, L. F.; Syutkina, O. P.; Shifrina, R. R.; Bogachev, Yu. S.; Zhuravleva, I. L.; Beletskaya, I. P. Izv. Akad. Nauk SSSR, Ser. Khim. 1983, 918; Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1983, 833.
55. (c) Rybakova, L. F.; Sigalov, A. B.; Syutkina, O. P.; Egorova, E. N.; Beletskaya, I. P. Izv. Akad. Nauk SSSR, Ser. Khim. 1981 ,2415; Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1981, 1995.
56. (c) Rybakova, L. F.; Sigalov, A. B.; Syutkina, O. P.; Egorova, E. N.; Beletskaya, I. P. Izv. Akad. Nauk SSSR, Ser. Khim. 1981 ,2415; Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1981, 1995.
57. The preparation of 1 was claimed by Inoe et al.: Inoe, N.; Jinno, M.; Shiomura, T. (Mitsui Toatsu Chemicals, Japan) JP 05059077 A2, 1993.
58. Chen, Y.-X.; Rausch, M. D.; Chien, J. C. W. J. Organomet. Chem. 1995, 497, 1.
59. For typical ranges of ring centroid-metal-ring centroid angles (119-130°) and inner angles at the bridging Si atom (93-104°), see refs 5e, 8b,i, 11c, and: Yoder, J. C.; Day, M. W.; Bercaw, J. E. Organometallics 1998, 17, 4946.
60. (a) Kowala, C.; Wailes, P. C.; Weigold, H.; Wunderlich, J. A. J. Chem. Soc., Chem. Commun. 1974, 993.
61. (b) Kowala, C.; Wunderlich, J. A. Acta Crystallogr. 1976, B32, 820.
62. Christopher, J. N.; Jordan, R. F.; Petersen, J. L.; Young, V. G., Jr. Organometallics 1997, 16, 3044.
63. (a) Könemann, M.; Erker, G.; Fröhlich, R.; Würthwein, E.-U. J. Am. Chem. Soc. 1997, 119, 11155.
64. (b) Mosges, G.; Hampel, F.; Schleyer, P. v. R. Organometallics 1992, 11, 1769.
65. (c) Brooks, J. J.; Rhine, W.; Stucky, G. D. J. Am. Chem. Soc. 1972, 94, 7339.
66. Resconi, L.; Piemontesi, F.; Camurati, I.; Sudmeijer, O.; Nifant'ev, I. E.; Ivchenko, P. V.; Kuz'mina, L. G. J. Am. Chem. Soc. 1998, 120, 2308.
67. den Haan, K. H.; de Boer, J. L.; Teuben, J. H.; Spek, A. L.; Kojić-Prodić, B.; Hays, G. R.; Huis, R. Organometallics 1986, 5, 1726.
68. 3 Y-N = 2.224(6) Å, see: Westernhausen, M.; Hartmann, M.; Pfitzner, A.; Schwarz, W. Z. Anorg. Allg. Chem. 1995, 621, 837.
69. 2] Y-N = 2.248(4)-2.265(4)Å, see ref 22a.
70. 2 = 2.255(8) Å, see: Mu, Y.; Piers, W. E.; MacDonald, M.-A.; Zaworotko, M. J. Can. J. Chem. 1995, 73, 2233.
71. 2 Y-N = 2.281(8) and 2.211(8) Å, see ref 11c.
72. 2 = 2.338(11) Å, Y-N(DAC) = 2.283(12), 2.29(2) Å, see: Lee, L.; Berg, D. J.; Bushnell, G. W. Inorg. Chem. 1994, 33, 5302.
73. 2 Y-N = 2.237(4) Å, see ref 11a.
74. Lauher, J. W.; Hoffmann, R. J. Am. Chem. Soc. 1976, 98, 1729.
75. (a) Evans, W. J.; Anwander, R.; Ziller, J. W.; Khan, S. I. Inorg. Chem. 1995, 34, 5927.
76. (b) Barnhart, D. M.; Clark, D. L.; Gordon, J. C.; Huffman, J. C.; Watkin, J. G.; Zwick, B. D. J. Am. Chem. Soc. 1993, 115, 8461.
77. (c) Heijden, H.; Schaverien, C.; Orpen, A. G. Organometallics 1989, 8, 255.
78. (d) Evans, W. J.; Drummond, D. K.; Zhang, H.; Atwood, J. L. Inorg. Chem. 1988, 27, 575,
79. (e) Tilley, T. D.; Andersen, R. A.; Zalkin, A. Inorg. Chem. 1984, 23, 2271.
80. (a) Schumann, H.; Rosenthal, E. C. E.; Kociok-Köhn, G.; Molander, G. A.; Winterfeld, J. J. Organomet. Chem. 1995, 496, 233.
81. (b) Evans, W. J.; Keyer, R. A.; Ziller, J. W. Organometallics 1993, 12, 2618.
82. MoleN, An Interactive Structure Solution Program; Enraf-Nonius, Delft, The Netherlands, 1994.
83. Sheldrick, G. M. SHELXL 93: Program for Crystal Structure Determination; University of Göttingen, Göttingen, Germany, 1993.