Neutral tripodal amidozirconium alkyls and hydride. Synthesis, structures, and catalytic olefin insertions

Organometallics

Volumn 19, Issue 6, 2000, Pages 963-965

  Jia, Li ^a   Ding, Errun ^a   Rheingold, Arnold L ^b   Rhatigan, Brian ^b  

^a LEHIGH UNIVERSITY   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000407861     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om991023t     Document Type: Article

References (55)

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14. Recent reviews of cationic metallocenes and olefin polymerization: (a) Abbenhuis, H. C. L. Angew. Chem., Int. Ed. 1999, 38, 1058. (b) McKnight, A. L.; Waymouth, R. M. Chem. Rev. 1998, 98, 2587. (c) Kaminsky, W. J. Chem. Soc., Datton Trans. 1998, 1413. (d) Montagna, A. A.; Dekmezian, A. H.; Burkhart, R. M. CHEMTECH 1997, 27, 26. (e) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (f) Brintzinger, H. H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (g) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (h) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325.
15. Recent reviews of cationic metallocenes and olefin polymerization: (a) Abbenhuis, H. C. L. Angew. Chem., Int. Ed. 1999, 38, 1058. (b) McKnight, A. L.; Waymouth, R. M. Chem. Rev. 1998, 98, 2587. (c) Kaminsky, W. J. Chem. Soc., Datton Trans. 1998, 1413. (d) Montagna, A. A.; Dekmezian, A. H.; Burkhart, R. M. CHEMTECH 1997, 27, 26. (e) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (f) Brintzinger, H. H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (g) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (h) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325.
16. Recent reviews of cationic metallocenes and olefin polymerization: (a) Abbenhuis, H. C. L. Angew. Chem., Int. Ed. 1999, 38, 1058. (b) McKnight, A. L.; Waymouth, R. M. Chem. Rev. 1998, 98, 2587. (c) Kaminsky, W. J. Chem. Soc., Datton Trans. 1998, 1413. (d) Montagna, A. A.; Dekmezian, A. H.; Burkhart, R. M. CHEMTECH 1997, 27, 26. (e) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (f) Brintzinger, H. H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (g) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (h) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325.
17. Recent reviews of cationic metallocenes and olefin polymerization: (a) Abbenhuis, H. C. L. Angew. Chem., Int. Ed. 1999, 38, 1058. (b) McKnight, A. L.; Waymouth, R. M. Chem. Rev. 1998, 98, 2587. (c) Kaminsky, W. J. Chem. Soc., Datton Trans. 1998, 1413. (d) Montagna, A. A.; Dekmezian, A. H.; Burkhart, R. M. CHEMTECH 1997, 27, 26. (e) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (f) Brintzinger, H. H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (g) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (h) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325.
18. Recent reviews of cationic metallocenes and olefin polymerization: (a) Abbenhuis, H. C. L. Angew. Chem., Int. Ed. 1999, 38, 1058. (b) McKnight, A. L.; Waymouth, R. M. Chem. Rev. 1998, 98, 2587. (c) Kaminsky, W. J. Chem. Soc., Datton Trans. 1998, 1413. (d) Montagna, A. A.; Dekmezian, A. H.; Burkhart, R. M. CHEMTECH 1997, 27, 26. (e) Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255. (f) Brintzinger, H. H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143. (g) Marks, T. J. Acc. Chem. Res. 1992, 25, 57. (h) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325.
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20. Cationic olefin polymerization catalysts containing amide ligands: (a) Liang, L.-C.; Schrock, R. R.; Davis, W. M.; McConville, D. H. J. Am. Chem. Soc. 1999, 121, 5797. (b) Guerin, F.; McConville, D. H.; Vittal, J. J.; Yap, G. A. P. Organometallics 1998, 17, 5172. (c) Wright, J. M.; Landis, C. R.; Ros, M. A. M. P.; Horton, A. D. Organometallics 1998, 17, 5031.
21. Cationic olefin polymerization catalysts containing amide ligands: (a) Liang, L.-C.; Schrock, R. R.; Davis, W. M.; McConville, D. H. J. Am. Chem. Soc. 1999, 121, 5797. (b) Guerin, F.; McConville, D. H.; Vittal, J. J.; Yap, G. A. P. Organometallics 1998, 17, 5172. (c) Wright, J. M.; Landis, C. R.; Ros, M. A. M. P.; Horton, A. D. Organometallics 1998, 17, 5031.
22. Cationic olefin polymerization catalysts containing amide ligands: (a) Liang, L.-C.; Schrock, R. R.; Davis, W. M.; McConville, D. H. J. Am. Chem. Soc. 1999, 121, 5797. (b) Guerin, F.; McConville, D. H.; Vittal, J. J.; Yap, G. A. P. Organometallics 1998, 17, 5172. (c) Wright, J. M.; Landis, C. R.; Ros, M. A. M. P.; Horton, A. D. Organometallics 1998, 17, 5031.
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24. Neutral group 4 compounds isoelectronic to cationic metallocenes have been demonstrated to catalyze ethylene polymerization and/or alkyne hydrogenation, see: (a) Pindado Jimnez, G.; Lancaster, S. J.; Thornton-Pett, M.; Bochmann, M. J. Am. Chem. Soc. 1998, 720, 6816. (b) Pastor, A. Kiely, A. F.; Henling, L. M.; Day, M. W.; Bercaw, J. E. J. Organomet. Chem. 1997, 528, 65. (c) Yoshida, M.; Crowther, D. J.; Jordan, R. F. Organometallics 1997, 16, 1349.
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43. 3).
44. 3, GOF = 1.994, R(F) = 8.83% for 15 270 observed independent reflections (4° ≤ 2θ ≤ 48°).
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46. 3).
47. In a typical experiment, catalyst 2 (30 mg, 44 μmol) was loaded into a 100 mL flask in the glovebox. The flask was attached to a vacuum line and evacuated, and toluene (∼20 mL) was condensed into the flask. The solution was exposed to ethylene (1 atm) and stirred for 72 h at 90°C. Methanol (2 mL) was added to quench the polymerization. The hot polymer solution was filtered to remove the decomposed catalyst and was then cooled to room temperature to precipitate the polymer. White polyethylene was collected by filtration, dried under vacuum, and weighed (97(±4) mg).
48. See Supporting Information for the 13C spectrum and assignments of the insertion products. The octyl derivative seems also to be present.
49. 3).
50. Alkene insertion into a Zr-H bond is common. For example, hydrozirconation: Schwartz, J. Pure Appl. Chem. 1980, 52, 733.
51. 3).
52. Diene cyclization: Barta, N. S.; Kirk, B. A.; Stille, J. R. J. Organomet. Chem. 1995, 487, 47.
53. 1, 5-Hexadiene polymerization: Coates, G. W.; Waymouth, R. M. J. Am. Chem. Soc. 1993, 115, 91, and references therein.
54. Mechansitic study of olefin insertion by diene cyclization: Grubbs, R. H.; Coates, G. W. Acc. Chem. Res. 1996, 29, 85.
55. 3).