Insertion of a platinum(0) fragment into the strained silicon-carbon bond of a silicon-bridged [1]ferrocenophane: Synthesis, alkyne insertion chemistry, and catalytic reactivity of the [2]platinasilaferrocenophane Fe(η5-C5H4)2Pt(PEt 3)2SiMe2

Journal of the Chemical Society - Dalton Transactions

Volumn , Issue 17, 1998, Pages 2799-2805

  Temple, Karen ^a   Lough, Alan J ^a   Sheridan, John B ^b   Manners, Ian ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b University Heights   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33749096198     PISSN: 03009246     EISSN: None     Source Type: Journal    
DOI: 10.1039/a801935e     Document Type: Article

References (89)

1. For late transition metal catalysts for the copolymerization of olefins and CO, see: C. M. Killian, D. J. Tempel, L. K. Johnson and M. Brookhart, J. Am. Chem. Soc., 1996, 118, 11 664;
2. L. K. Johnson, C. M. Killian and M. Brookhart, J. Am. Chem. Soc., 1995, 117, 6414;
3. A. Sen, J. T. Chen, W. M. Vetter and R. R. Whittle, J. Am. Chem. Soc., 1987, 109, 148;
4. F. C. Rix, M. Brookhart and P. S. White, J. Am. Chem. Soc., 1996, 118, 4746;
5. S. Bronco, G. Consiglio, R. Hutter, A. Batistini and U. W. Suter, Macromolecules, 1994, 27, 4436.
6. R. F. Jordan, J. Organomet. Chem., 1991, 32, 325 and refs. therein.
7. See for example: B. P. S. Chauhan, T. Simizu and M. Tanaka, Chem. Lett., 1997, 785;
8. J. A. Reichl, C. M. Popoff, L. A. Gallagher, E. E. Remsen and D. H. Berry, J. Am. Chem. Soc., 1996, 118, 9450;
9. V. K. Dioumaev and J. F. Harrod, J. Organomet. Chem., 1996, 521, 133;
10. T. Imori, R. H. Heyn, T. D. Tilley and A. L. Rheingold, J. Organomet. Chem., 1995, 493, 83.
11. See for example: J. R. Babcock and L. R. Sita, J. Am. Chem. Soc., 1996, 118, 12 481;
12. V. Lu and T. D. Tilley, Macromolecules, 1996, 29, 5763;
13. T. Imori, V. Lu, H. Cai and T. D. Tilley, J. Am. Chem. Soc., 1995, 117, 9931;
14. T. Imori and T. D. Tilley, J. Chem. Soc., Chem. Commun., 1993, 1607.
15. C. S. Cundy and M. F. Lappert, J. Chem. Soc., Dalton Trans., 1978, 655 and refs. therein;
16. D. R. Weyenberg and L. E. Nelson, J. Org. Chem., 1965, 30, 2618;
17. H. Yamashita, M. Tanaka and K. Honda, J. Am. Chem. Soc., 1995, 117, 8873.
18. L. V. Interrante, H. J. Wu, T. Apple, Q. Shen, B. Ziemann and D. M. Narsavage, J. Am. Chem. Soc., 1994, 116, 12 085;
19. H. J. Wu and L. V. Interrante, Macromolecules, 1992, 25, 1840.
20. D. A. Foucher, B.-Z. Tang and I. Manners, J. Am. Chem. Soc., 1992, 114, 6246.
21. I. Manners, Adv. Organomet. Chem., 1995, 37, 131;
22. I. Manners, Can. J. Chem., 1998, 76, 731.
23. R. Bayer, T. Pöhlmann and O. Nuyken, Makromol. Chem., Rapid Commun., 1993, 14, 359;
24. M. Altman and U. H. F. Bunz, Angew. Chem., Int. Ed. Engl., 1995, 34, 569;
25. P. F. Brandt and T. B. Rauchfuss, J. Am. Chem. Soc., 1992, 114, 1926;
26. M. Rosenblum, H. M. Nugent, K.-S. Jang, M. M. Labes, W. Cahalane, P. Klemarczyk and W. M. Reiff, Macromolecules, 1995, 28, 6330;
27. M. Morán, M. C. Pascual, I. Cuadrado and J. Losada, Organometallics, 1993, 12, 811;
28. I. Cuadrado, M. Móran, C. M. Casado, B. Alonso, F. Lobete, B. Garcia, M. Ibisate and J. Losada, Organometallics, 1996, 15, 5278;
29. G. E. Sourthard, M. D. Curtis and J. W. Kampf, Organometallics, 1996, 15, 4667;
30. R. N. Kapoor, G. M. Crawford, J. Mahmoud, V. V. Dementiev, M. T. Nguyen, A. F. Diaz and K. H. Pannell, Organometallics, 1996, 15, 2848;
31. T. M. Alias, S. Barlow, J. S. Tudor, D. O'Hare, R. T. Perry, J. M. Nelson and I. Manners, J. Organomet. Chem., 1997, 528, 42.
32. Y. Ni, R. Rulkens, J. K. Pudelski and I. Manners, Makromol. Chem., Rapid Commun., 1995, 16, 637.
33. N. P. Reddy, H. Yamashita and M. Tanaka, J. Chem. Soc., Chem. Commun., 1995, 2263.
34. N. P. Reddy, N. Choi, S. Shimada and M. Tanaka, Chem. Lett., 1996, 649.
35. P. Gómez-Elipe, P. M. Macdonald and I. Manners, Angew. Chem., Int. Ed. Engl., 1997, 36, 762.
36. R. Rulkens, Y. Ni and I. Manners, J. Am. Chem. Soc., 1994, 116, 12 121.
37. R. Resendes, P. Nguyen, A. J. Lough and I. Manners, Chem. Commun., 1998, 1001.
38. W. R. Bamford, J. C. Lovie and J. A. C. Watt, J. Chem. Soc. C, 1966, 1137.
39. C. S. Cundy, C. Eaborn and M. F. Lappert, J. Organomet. Chem., 1972, 44, 291.
40. For the insertion of Fe into a silacyclobutane see: C. S. Cundy and M. F. Lappert, J. Chem. Soc., Chem. Commun., 1972, 445;
41. C. S. Cundy and M. F. Lappert, J. Chem. Soc., Dalton Trans., 1976, 910;
42. C. S. Cundy and M. F. Lappert, J. Chem. Soc., Dalton Trans., 1978, 665.
43. For insertion of Pt and/or Pd into a silacyclobutane: H. Yamashita, M. Tanaka and K. Honda, J. Am. Chem. Soc., 1995, 117, 8873;
44. Y. Tanaka, H. Yamashita, S. Shimada and M. Tanaka, Organometallics, 1997, 16, 3246;
45. P. Braunstein and M. Knorr, J. Organomet. Chem., 1995, 500, 21.
46. J. B. Sheridan, A. J. Lough and I. Manners, Organometallics, 1996, 15, 2195.
47. N. P. Reddy, H. Yamashita and M. Tanaka, J. Chem. Soc., Chem. Commun., 1995, 2263.
48. T. J. Peckham, J. Massey, M. Edwards, I. Manners and D. Foucher, Macromolecules, 1996, 29, 2296.
49. J. B. Sheridan, P. Gómez-Elipe and I. Manners, Makromol. Chem., Rapid. Commun., 1996, 17, 319.
50. H. Yamashita, M. Tanaka and K. Honda, J. Am. Chem. Soc., 1995, 117, 8873.
51. J. L. Speier, Adv. Organomet. Chem., 1979, 407;
52. I. Ojima, in The Chemistry of Organic Silicon Compounds, eds. S. Patai and Z. Rappoport, Wiley, Chichester, 1989, p. 1479;
53. A. J. Chalk and J. F. Harrod. J. Am. Chem. Soc., 1965, 87, 16;
54. J. F. Harrod and A. J. Chalk, J. Am. Chem. Soc., 1965, 87, 1133;
55. M. A. Schroeder and M. S. Wrighton, J. Organomet. Chem., 1977, 128, 345;
56. R. G. Austin, R. S. Paonessa, P. J. Giordano and M. S. Wrighton, ACS Symp. Ser., 1978, 169, 189;
57. B. Marciniec and J. Gulinski, J. Organomet. Chem., 1983, 252, 349;
58. C. L. Randolph and M. S. Wrighton, J. Am. Chem. Soc., 1986, 108, 3366.
59. M. Murakami, T. Yoshida and Y. Ito, Organometallics, 1994, 13, 2900.
60. See for example: W. S. Palmer and K. A. Woerpel, Organometallics, 1997, 16, 1097;
61. A. Naka, S. Okazaki, M. Hayashi and M. Ishikawa, J. Organomet. Chem, 1995, 499, 35;
62. W. S. Palmer and K. A. Woerpel, Organometallics, 1997, 16, 4827.
63. For insertion of alkynes into Si-Si bonds: H. Okinoshima, K. Yamamoto and M. Kumada, J. Am. Chem. Soc., 1972, 94, 9263;
64. H. Okinoshima, K. Yamamoto and M. Kumada, J. Organomet. Chem., 1975, 86, C27;
65. H. Sakurai, K. Kamiyama and Y. Nakadaira, J. Am. Chem. Soc., 1975, 97, 931;
66. H. Yamashita, M. Catellani and M. Tanaka, Chem. Lett., 1991, 241;
67. H. Watanabe, M. Kobayashi, K. Higuchi and Y. Nagai, J. Organomet. Chem., 1980, 186, 51;
68. C. Liu and C. Cheng, J. Am. Chem. Soc., 1975, 97, 6746;
69. C. W. Carlson and R. West, Organometallics, 1983, 2, 1801;
70. D. Seyferth, E. W. Goldman and J. Escudie, J. Organomet. Chem., 1984, 271, 337;
71. M. Murakami, T. Yoshida and Y. Ito, Organometallics, 1994, 13, 2900.
72. W. Finckh, B. Z. Tang, A. Lough and I. Manners, Organometallics, 1992, 11, 2904.
73. For reactivity of alkynes towards a Pt-Si bond: J. Chatt, C. Eaborn and P. N. Kapoor, J. Organomet. Chem., 1970, 23, 109;
74. H. Yamashita, M. Tanaka and M. Goto, Organometallics, 1993, 12, 988;
75. H. Yamashita, M. Tanaka and M. Goto, Organometallics, 1992, 11, 3227;
76. F. Glockling and K. A. Gooton, J. Chem. Soc. A, 1967, 1066;
77. C. Eaborn, T. N. Metham and A. Pidcock, J. Organomet. Chem., 1973, 63, 107;
78. C. Eaborn, D. J. Tune and A. Pidcock, J. Chem. Soc., Dalton Trans., 1973, 2255;
79. C. Eaborn, B. Ratcliff and A. Pidcock, J. Organomet. Chem., 1974, 65, 181;
80. C. Eaborn, T. N. Metham and A. Pidcock, J. Organomet. Chem., 1977, 131, 377.
81. J. B. Sheridan, K. Temple, A. J. Lough and I. Manners, J. Chem. Soc., Dalton Trans., 1997, 711.
82. P. Gomez-Elipe and I. Manners, unpublished work.
83. Gel-permeation chromatography gives molecular weight data based on the hydrodynamic size of polymer molecules. Oxidation of the ferrocene units leads to contraction of the polymer coils due to poorer polymer/solvent interactions and so an apparent decrease in molecular weight is detected. For an introduction to GPC, see R. J. Young and P. A. Lovell, Introduction to Polymers, Chapman and Hall, 2nd edn., 1991, pp. 211-221.
84. R. Rulkens, A. J. Lough and I. Manners, J. Am. Chem. Soc., 1994, 116, 797;
85. R. Rulkens, A. J. Lough and I. Manners. J. Am. Chem. Soc., 1996, 118, 12 683.
86. I. Manners, Polyhedron, 1996, 15, 4311.
87. N. P. Reddy, T. Hayashi and M. Tanaka, Chem. Commun., 1996, 1865.
88. M. F. Summers, L. G. Marzilli and A. Bax, J. Am. Chem. Soc., 1986, 108, 4285.
89. G. M. Sheldrick, SHELXTL PC, Siemens Analytical X-Ray Instruments Inc., Madison, WI, 1994.