Activation of 2,6-bis(imino)pyridine iron(II) chloride complexes by methylaluminoxane: An electrospray ionization tandem mass spectrometry investigation

Organometallics

Volumn 24, Issue 15, 2005, Pages 3664-3670

  Castro, Pascal M ^a   Lahtinen, Petro ^a   Axenov, Kirill ^a   Viidanoja, Jyrki ^a   Kotiaho, Tapio ^a   Leskelä, Markku ^a   Repo, Timo ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; DECOMPOSITION; IONIZATION; IRON COMPOUNDS; MASS SPECTROMETRY; ULTRAVIOLET RADIATION;

ELECTROSPRAY IONIZATION; METALLOCENE CATALYSTS; METHYLALUMINOXANE (MAO); TETRAHYDROFURAN (THF);

ORGANOMETALLICS;

EID: 22944442587     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om050351s     Document Type: Article

References (60)

1. (a) Britovsek, G. J. P.; Gibson, V. C.; Wass, D. F. Angew. Chem., Int. Ed. 1999, 38, 428-447.
2. (b) Ittel, S. D.; Johnson, L. K.; Brookhart, M. Chem. Rev. 2000, 100, 1169-1203.
3. (c) Gibson, V. C.; Spitzmesser, S. K. Chem. Rev. 2003, 103, 283-315.
4. (a) Britovsek, G. J. P.; Bruce, M.; Gibson, V. C.; Kimberley, B. S.; Maddox, P. J.; Mastroianni, S.; McTavish, S. J.; Redshaw, C.; Solan, G. A.; Strömberg, S.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1999, 121, 8728-8740.
5. (b) Small, B. L.; Brookhart, M. Macromolecules 1999, 32, 2120-2130.
6. For metal complex activation by Lewis acid compounds in general, see: (a) Chen, E. Y. X.; Marks, T. J. Chem. Rev. 2000, 100, 1391-1434.
7. (b) Coevoet, D.; Cramail, H.; Deffieux, A.; Mladenov, C.; Pedeutour, J. N.; Peruch, F. Polym. Int. 1999, 48, 257-263.
8. (a) Griffiths, E. A. H.; Britovsek, G. J. P.; Gibson, V. C.; Gould, I. R. Chem. Commun. 1999, 1333-1334.
9. (b) Deng, L.; Margl, P.; Ziegler, T. J. Am. Chem. Soc. 1999, 121, 6479-6487.
10. (c) Khoroshun, D. V.; Musaev, D. G.; Vreven, T.; Morokuma, K. Organometallics 2001, 20, 2007-2026.
11. Kaminsky, W.; Strübel, C. J. Mol. Catal. A: Chem. 1998, 128, 191-200.
12. (a) Yamamoto, A.; Morifuji, K.; Ikeda, S.; Saito, T.; Uchida, Y.; Misono, A. J. Am. Chem. Soc. 1965, 87, 4652-4653.
13. (b) Yamamoto, A.; Morifuji, K.; Ikeda, S.; Saito, T.; Uchida, Y.; Misono, A. J. Am. Chem. Soc. 1968, 90, 1878-1883.
14. (c) Lau, W.; Huffman, J. C.; Kochi, J. K. Organometallics 1982, 1, 155-169.
15. (d) Field, L. D.; Messerle, B. A.; Smernik, R. J.; Hambley, T. W.; Turner, P. Inorg. Chem. 1997, 36, 2884-2892.
16. (e) Bennett, M. A.; Ditzel, E. J.; Hunter, A. D.; Khan, K.; Kopp, M. R.; Neumann, H.; Robertson, G. B.; Zeh, H. Dalton 2000, 1733-1741.
17. (a) Ikariya, T.; Yamamoto, A. J. Chem. Soc., Chem. Commun. 1974, 720.
18. (b) Ikariya, T.; Yamamoto, A. J. Organomet. Chem. 1976, 118, 65-78.
19. (a) Bart, S. C.; Hawrelak, E. J.; Schmisseur, A. K.; Lobkovsky, E.; Chirik, P. J. Organometallics 2004, 23, 237-246.
20. (b) Vela, J.; Vaddadi, S.; Cundari, T. R.; Smith, J. M.; Gregory, E. A.; Lachicotte, R. J.; Flaschenriem, C. J.; Holland, P. L. Organometallics 2004, 23, 5226-5239.
21. (c) Hermes, A. R.; Girolami, G. S. Organometallics 1987, 6, 763-768.
22. Britovsek, G. J. P.; Gibson, V. C.; Spitzmesser, S. K.; Tellmann, K. P.; White, A. J. P.; Williams, D. J. J. Dalton 2002, 6, 1159-1171.
23. Babik, S. T.; Fink, G. J. Mol. Catal. A: Chem. 2002, 188, 245-253.
24. (a) Bochmann, M.; Lancaster, S. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1634-1637.
25. (b) Tritto, I.; Donetti, R.; Sacchi, M. C.; Locatelli, P.; Zannoni, G. Macromolecules 1997, 30, 1247-1252.
26. (c) Petros, R. A.; Norton, J. R. Organometallics 2004, 23, 5105-5107.
27. (a) Talsi, E. P.; Babushkin, D. E.; Semikolenova, N. V.; Zudin, V. N.; Panchenko, V. N.; Zakharov, V. A. Macromol. Chem. Phys. 2001, 202, 2046-2051.
28. (b) Bryliakov, K. P.; Semikolenova, N. V.; Zudin, V. N.; Zakharov, V. A.; Talsi, E. P. Catal. Commun. 2004, 5, 45-48.
29. (c) Bryliakov, K. P.; Semikolenova, N. V.; Zakharov, V. A.; Talsi, E. P. Organometallics 2004, 23, 5375-5378.
30. Britovsek, G. J. P.; Cohen, S. A; Gibson, V. C.; van Meurs, M. J. Am. Chem. Soc. 2004, 126, 10701-10712.
31. 12a
32. (a) Whitehouse, C. M.; Dreyer, R. N.; Yamashita, M.; Fenn, J. B. Anal. Chem. 1985, 57, 675-679.
33. (b) Fenn, J. B.; Mann, M.; Meng, C. K.; Wong, S. F.; Whitehouse, C. M. Science 1989, 246, 64-71.
34. (c) Vestal, M. L. Chem. Rev. 2001, 101, 361-375.
35. Lipshutz, B. H.; Stevens, K. L.; James, B.; Pavlovich, J. G. J. Am. Chem. Soc. 1996, 118, 6796-6797.
36. (a) Aliprantis, A. O.; Canary, J. W. J. Am. Chem. Soc. 1994, 116, 6985-6986.
37. (b) Sabino, A. A.; Machado, A. H. L.; Correia, C. R. D.; Eberlin, M. N. Angew. Chem., Int. Ed. 2004, 43, 2514-2518.
38. Feichtinger, D.; Plattner, D. A.; Chen, P. J. Am. Chem. Soc. 1998, 120, 7125-7126.
39. (a) Chen, P. Angew. Chem., Int. Ed. 2003, 42, 2832-2847.
40. (b) Hinderlingg, C.; Chen, P. Angew. Chem., Int. Ed. Engl. 1999, 38, 2253-2256.
41. Castro, P. M.; Lappalainen, K.; Ahlgrén, M.; Leskelä, M.; Repo, T. J. Polym. Sci. Part A: Polym. Chem. 2003, 41, 1380-1389.
42. Castro, P. M.; Lankinen, M. P.; Uusitalo, A. M.; Leskelä, M.; Repo, T. Macromol. Symp. 2004, 213, 199-208.
43. 9
44. Coevoet, D.; Cramail, H.; Deffieux, A. Macromol. Chem. Phys. 1998, 199, 1451-1457.
45. Britovsek, G. J. P.; Clentsmith, G. K. B.; Gibson, V. C.; Goodgame, D. M. L.; McTavish, S. J.; Pankhurst, Q. A. Catal. Comm. 2002, 3, 207-211.
46. (a) Jordan, R. F.; Dasher, W. E.; Echols, S. F. J. Am. Chem. Soc. 1986, 108, 1718-1719.
47. (b) Jordan, R. F.; Bajgur, C. S.; Willett, R.; Scott, B. J. Am. Chem. Soc. 1986, 108, 7410-7411.
48. (c) Jordan, R. F.; LaPointe, R. E:; Bradley, P. K; Baenziger, N. Organometallics 1989, 8, 2892-2903.
49. 2 by addition of TMA to a monometallic zirconocenium species was expressed by a progressive hypsochromic shift of the MLCT band; see: Coevoet, D.; Cramail, H.; Deffieux, A. Macromol. Chem. Phys. 1998, 199, 1459-1464.
50. (a) Kaminsky, W.; Steiger, R. Polyhedron 1988, 7, 2375-2381.
51. (b) Kaminsky, W.; Strübel, C. J. Mol. Catal. A: Chem. 1998, 128, 191-200.
52. (c) Kaminsky, W. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 3911-3921.
53. + and TMA were observed in the gas phase by Fourier transform ion cyclotron resonance mass spectroscopy; see: Siedle, A. R.; Newmark, R. A.; Schroepfer, J. N.; Lyon, P. A. Organometallics 1991, 10, 400-404.
54. According to our unpublished results, MAO-activated 2,6-bis-(imino) pyridine iron(II) chloride complexes are able to provide, although to a minor extent, the ring-opening polymerization of THF in the presence of acrylate monomers, which further supports the feasibility of the reaction discussed here.
55. (a) Fiedler, A.; Schröder, D.; Scharwz, H.; Tjelta, B. L.; Armentrout, P. B. J. Am. Chem. Soc. 1996, 118, 5047-5055.
56. (b) Kirkwood, D. A.; Stace, A. J. Int. J. Mass Spectrom. Ion Processes 1997, 171, 39-49.
57. 2a as it produces low molar mass polyethylene with low catalytic activity; see: Bruce, M.; Gibson, V. C.; Redshaw, C.; Solan, G. A.; White, A. J. P.; Williams, D. J. Chem. Commun. 1998, 2523-2524.
58. (b) Baugh, L. S.; Sissano, J. A. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 1633-1651.
59. Kim, J. S.; Wojcinski, L. M., II; Liu, S.; Sworen, J. C.; Sen, A. J. Am. Chem. Soc. 2000, 122, 5668-5669.
60. 3 has been reported; see: Beck, S.; Prosenc, M. H.; Brintzinger, H. H. J. Mol. Catal. A: Chem. 1998, 128, 41-52.