Synthesis, structures, and properties of strained spirocyclic [1]sila- and [1]germaferrocenophanes and tetraferrocenylsilane

Organometallics

Volumn 17, Issue 9, 1998, Pages 1873-1883

  MacLachlan, Mark J ^a   Lough, Alan J ^a   Geiger, William E ^b   Manners, Ian ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b UNIVERSITY OF VERMONT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001452986     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om971071i     Document Type: Article

References (55)

1. For recent examples of transition-metal-based polymeric materials, see, for example: (a) Pittman, C. U.; Carraher, C. E.; Zeldin, M.; Sheats, J. E.; Culbertson, B. M., Eds. Metal-Containing Polymeric Materials; Plenum Press: New York, 1996. (b) Altman, M.; Bunz, U. H. F. Angew. Chem., Int. Ed. Engl. 1995, 34, 569. (c) Rosenblum, M.; Nugent, H. M.; Jang, K.-S.; Labes, M. M.; Cahalane, W.; Klemarczyk, P.; Reiff, W. M. Macromolecules 1995, 28, 6330. (d) Chen, H.; Archer, R. D. Macromolecules 1995, 28, 1609. (e) Stanton, C. E.; Lee, T. R.; Grubbs, R. H.; Lewis, N. S.; Pudelski, J. K.; Callstrom, M. R.; Erickson, M. S.; McLaughlin, M. L. Macromolecules 1995, 28, 8713. (f) Buretea, M. A.; Tilley, T. D. Organometallics 1997, 16, 1507. (g) Southard, G. E.; Curtis, M. D. Organometallics 1997, 16, 5618.
2. For recent examples of transition-metal-based polymeric materials, see, for example: (a) Pittman, C. U.; Carraher, C. E.; Zeldin, M.; Sheats, J. E.; Culbertson, B. M., Eds. Metal-Containing Polymeric Materials; Plenum Press: New York, 1996. (b) Altman, M.; Bunz, U. H. F. Angew. Chem., Int. Ed. Engl. 1995, 34, 569. (c) Rosenblum, M.; Nugent, H. M.; Jang, K.-S.; Labes, M. M.; Cahalane, W.; Klemarczyk, P.; Reiff, W. M. Macromolecules 1995, 28, 6330. (d) Chen, H.; Archer, R. D. Macromolecules 1995, 28, 1609. (e) Stanton, C. E.; Lee, T. R.; Grubbs, R. H.; Lewis, N. S.; Pudelski, J. K.; Callstrom, M. R.; Erickson, M. S.; McLaughlin, M. L. Macromolecules 1995, 28, 8713. (f) Buretea, M. A.; Tilley, T. D. Organometallics 1997, 16, 1507. (g) Southard, G. E.; Curtis, M. D. Organometallics 1997, 16, 5618.
3. For recent examples of transition-metal-based polymeric materials, see, for example: (a) Pittman, C. U.; Carraher, C. E.; Zeldin, M.; Sheats, J. E.; Culbertson, B. M., Eds. Metal-Containing Polymeric Materials; Plenum Press: New York, 1996. (b) Altman, M.; Bunz, U. H. F. Angew. Chem., Int. Ed. Engl. 1995, 34, 569. (c) Rosenblum, M.; Nugent, H. M.; Jang, K.-S.; Labes, M. M.; Cahalane, W.; Klemarczyk, P.; Reiff, W. M. Macromolecules 1995, 28, 6330. (d) Chen, H.; Archer, R. D. Macromolecules 1995, 28, 1609. (e) Stanton, C. E.; Lee, T. R.; Grubbs, R. H.; Lewis, N. S.; Pudelski, J. K.; Callstrom, M. R.; Erickson, M. S.; McLaughlin, M. L. Macromolecules 1995, 28, 8713. (f) Buretea, M. A.; Tilley, T. D. Organometallics 1997, 16, 1507. (g) Southard, G. E.; Curtis, M. D. Organometallics 1997, 16, 5618.
4. For recent examples of transition-metal-based polymeric materials, see, for example: (a) Pittman, C. U.; Carraher, C. E.; Zeldin, M.; Sheats, J. E.; Culbertson, B. M., Eds. Metal-Containing Polymeric Materials; Plenum Press: New York, 1996. (b) Altman, M.; Bunz, U. H. F. Angew. Chem., Int. Ed. Engl. 1995, 34, 569. (c) Rosenblum, M.; Nugent, H. M.; Jang, K.-S.; Labes, M. M.; Cahalane, W.; Klemarczyk, P.; Reiff, W. M. Macromolecules 1995, 28, 6330. (d) Chen, H.; Archer, R. D. Macromolecules 1995, 28, 1609. (e) Stanton, C. E.; Lee, T. R.; Grubbs, R. H.; Lewis, N. S.; Pudelski, J. K.; Callstrom, M. R.; Erickson, M. S.; McLaughlin, M. L. Macromolecules 1995, 28, 8713. (f) Buretea, M. A.; Tilley, T. D. Organometallics 1997, 16, 1507. (g) Southard, G. E.; Curtis, M. D. Organometallics 1997, 16, 5618.
5. For recent examples of transition-metal-based polymeric materials, see, for example: (a) Pittman, C. U.; Carraher, C. E.; Zeldin, M.; Sheats, J. E.; Culbertson, B. M., Eds. Metal-Containing Polymeric Materials; Plenum Press: New York, 1996. (b) Altman, M.; Bunz, U. H. F. Angew. Chem., Int. Ed. Engl. 1995, 34, 569. (c) Rosenblum, M.; Nugent, H. M.; Jang, K.-S.; Labes, M. M.; Cahalane, W.; Klemarczyk, P.; Reiff, W. M. Macromolecules 1995, 28, 6330. (d) Chen, H.; Archer, R. D. Macromolecules 1995, 28, 1609. (e) Stanton, C. E.; Lee, T. R.; Grubbs, R. H.; Lewis, N. S.; Pudelski, J. K.; Callstrom, M. R.; Erickson, M. S.; McLaughlin, M. L. Macromolecules 1995, 28, 8713. (f) Buretea, M. A.; Tilley, T. D. Organometallics 1997, 16, 1507. (g) Southard, G. E.; Curtis, M. D. Organometallics 1997, 16, 5618.
6. For recent examples of transition-metal-based polymeric materials, see, for example: (a) Pittman, C. U.; Carraher, C. E.; Zeldin, M.; Sheats, J. E.; Culbertson, B. M., Eds. Metal-Containing Polymeric Materials; Plenum Press: New York, 1996. (b) Altman, M.; Bunz, U. H. F. Angew. Chem., Int. Ed. Engl. 1995, 34, 569. (c) Rosenblum, M.; Nugent, H. M.; Jang, K.-S.; Labes, M. M.; Cahalane, W.; Klemarczyk, P.; Reiff, W. M. Macromolecules 1995, 28, 6330. (d) Chen, H.; Archer, R. D. Macromolecules 1995, 28, 1609. (e) Stanton, C. E.; Lee, T. R.; Grubbs, R. H.; Lewis, N. S.; Pudelski, J. K.; Callstrom, M. R.; Erickson, M. S.; McLaughlin, M. L. Macromolecules 1995, 28, 8713. (f) Buretea, M. A.; Tilley, T. D. Organometallics 1997, 16, 1507. (g) Southard, G. E.; Curtis, M. D. Organometallics 1997, 16, 5618.
7. For recent examples of transition-metal-based polymeric materials, see, for example: (a) Pittman, C. U.; Carraher, C. E.; Zeldin, M.; Sheats, J. E.; Culbertson, B. M., Eds. Metal-Containing Polymeric Materials; Plenum Press: New York, 1996. (b) Altman, M.; Bunz, U. H. F. Angew. Chem., Int. Ed. Engl. 1995, 34, 569. (c) Rosenblum, M.; Nugent, H. M.; Jang, K.-S.; Labes, M. M.; Cahalane, W.; Klemarczyk, P.; Reiff, W. M. Macromolecules 1995, 28, 6330. (d) Chen, H.; Archer, R. D. Macromolecules 1995, 28, 1609. (e) Stanton, C. E.; Lee, T. R.; Grubbs, R. H.; Lewis, N. S.; Pudelski, J. K.; Callstrom, M. R.; Erickson, M. S.; McLaughlin, M. L. Macromolecules 1995, 28, 8713. (f) Buretea, M. A.; Tilley, T. D. Organometallics 1997, 16, 1507. (g) Southard, G. E.; Curtis, M. D. Organometallics 1997, 16, 5618.
8. Manners, I. Angew. Chem., Int. Ed. Engl. 1996, 35, 1602.
9. (a) Brandt, P. F.; Rauchfuss, T. B. J. Am. Chem. Soc. 1992, 114, 1926.
10. (b) Compton, D. L.; Brandt, P. F.; Rauchfuss, T. B.; Rosenbaum, D. F.; Zukoski, C. F. Chem. Mater. 1995, 7, 2342.
11. Nugent, H. M.; Rosenblum, M.; Klemarczyk, P. J. Am. Chem. Soc. 1993, 115, 3848.
12. Foucher, D. A.; Tang, B.-Z.; Manners, I. J. Am. Chem. Soc. 1992, 114, 6246.
13. (a) Ni, Y.; Rulkens, R.; Manners, I. J. Am. Chem. Soc. 1996, 118, 4102.
14. (b) Ni, Y.; Rulkens, R.; Pudelski, J. K.; Manners, I. Macromol. Rapid Commun. 1995, 16, 637.
15. (c) Reddy, N. P.; Yamashita, H.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1995, 2263.
16. Manners, I. Adv. Organomet. Chem. 1995, 37, 131.
17. (a) Rulkens, R.; Resendes, R.; Verma, A.; Manners, I.; Murti, K.; Fossum, E.; Miller, P.; Matyjaszewski, K. Macromolecules 1997, 30, 8165.
18. (b) Liu, X.-H.; Bruce, D. W.; Manners, I. Chem. Commun. 1997, 289.
19. (c) Pudelski, J. K.; Rulkens, R.; Foucher, D. A.; Lough, A. J.; Macdonald, P. M.; Manners, I. Macromolecules 1995, 28, 7301.
20. (d) Pudelski, J. K.; Foucher, D. A.; Honeyman, C. H.; Macdonald, P. M.; Manners, I.; Barlow, S.; O'Hare, D. Macromolecules 1996, 29, 1894.
21. (e) MacLachlan, M. J.; Aroca, P.; Coombs, N.; Manners, I.; Ozin, G. A. Adv. Mater. 1998, 10, 144.
22. (a) Nguyen, M. T.; Diaz, A. F.; Dement'ev, V. V.; Pannell, K. H. Chem. Mater. 1993, 5, 1389.
23. (b) Tanaka, M.; Hayashi, T. Bull. Chem. Soc. Jpn. 1993, 66, 334.
24. (c) Barlow, S.; Rohl, A. L.; Shi, S.; Freeman, C. M.; O'Hare, D. J. Am. Chem. Soc. 1996, 118, 7578.
25. (d) Hmyene, M.; Yassar, A.; Escorne, M.; Percheron-Guegan, A.; Gamier, F. Adv. Mater. 1994, 6, 564.
26. Tatsuma, T.; Takada, K.; Matsui, H.; Oyama, N. Macromolecules 1994, 27, 6687.
27. MacLachlan, M. J.; Lough, A. J.; Manners, I. Macromolecules 1996, 29, 8562.
28. MacLachlan, M. J.; Kulbaba, K.; Manners, I. Manuscript in preparation.
29. Osborne, A. G.; Whiteley, R. H. J. Organomet. Chem. 1975, 101, C27.
30. Osborne, A. G.; Whiteley, R. H.; Meads, R. E. J. Organomet. Chem. 1980, 193, 345.
31. Blake, A. J.; Mayers, F. R.; Osborne, A. G.; Rosseinsky, D. R. J. Chem. Soc., Dalton Trans. 1982, 2379.
32. Rosseinsky, D. R.; Osborne, A. G.; Mayers, F. R. Opt. Mater. 1996, 6, 83.
33. Rosenberg, H. U.S. Patent 3,410,883, 1968; Chem. Abstr. 1969, 13149w.
34. Elschenbroich, C.; Bretschneider-Hurley, A.; Hurley, J.; Behrendt, A.; Massa, W.; Wocadlo, S.; Reijerse, E. Inorg. Chem. 1995, 34, 743.
35. Ushakov, N. V.; Finkel'shtein, E. S.; Babich, E. D. Polym. Sci., Ser. A 1995, 37, 320.
36. Finckh, W.; Tang, B.-Z.; Foucher, D. A.; Zamble, D. B.; Ziembinski, R.; Lough, A.; Manners, I. Organometallics 1993, 12, 823.
37. Foucher, D. A.; Edwards, M.; Burrow, R. A.; Lough, A. J.; Manners, I. Organometallics 1994, 13, 4959.
38. Roberts, R. M. G.; Silver, J.; Ranson, R. J.; Morrison, I. E. G. J. Organomet. Chem. 1981, 219, 233.
39. We define the ring pucker as the angle between the plane defined by Si, C(11), and C(13) and the plane defined by C(11), C(12), and C(13). Thus, it quantifies the fold in the silacyclobutane ring.
40. Mastryukov, V. S.; Dorefeeva, O. V.; Vilkov, L. V.; Cyvin, S. J.; Cyvin, B. N. J. Struct. Chem. (Engl. Transl.) 1975, 16, 438.
41. Pudelski, J. K.; Foucher, D. A.; Honeyman, C. H.; Lough, A. J.; Manners, I.; Barlow, S.; O'Hare, D. Organometallics 1995, 14, 2470.
42. Brown, G. M.; Meyer, T. J.; Cowan, D. O.; Levanda, C.; Kaufman, F.; Roling, P. V.; Raush, M. D. Inorg. Chem. 1975, 14, 506.
43. For leading references, see: Tendero, M. J. L.; Benito, A.; Cano, J.; Lloris, J. M.; Martinez-Manez, R.; Soto, J.; Edwards, A. J.; Raithby, P. R.; Rennie, M. A. J. Chem. Soc., Chem. Commun. 1995, 1643.
44. Steiger, B.; Shi, C.; Anson, F. C. Inorg. Chem. 1993, 32, 2107.
45. Sokol, W. F.; Evans, D. H.; Niki, K.; Yagi, T. J. Electroanal. Chem. Interfacial Electrochem. 1980, 108, 107.
46. Reike, R. D.; Tucker, I.; Milligan, S. N.; Wright, D. R.; Willeford, B. R.; Radnovich, L. J.; Eyring, M. W. Organometallics 1982, 1, 938.
47. Cowan, D. O.; Shu, P.; Hedberg, F. L.; Rossi, M.; Kistenmacher, T. J. J. Am. Chem. Soc. 1979, 101, 1304.
48. Long, T. V., Jr.; Huege, F. R. Chem. Commun. 1968, 1239.
49. Butler, I. S.; Harvey, P. D.; Allen, G. C. J. Raman Spectrosc. 1987, 18, 1.
50. Phillips, L.; Lacey, A. R.; Cooper, M. K. J. Chem. Soc., Dalton Trans. 1988, 1383.
51. Rausch, M. D.; Ciappenelli, D. J. J. Organomet. Chem. 1967, 10, 5025.
52. Guillaneux, D.; Kagan, H. B. J. Org. Chem. 1995, 60, 2502.
53. Bishop, J. J.; Davison, A.; Katcher, M. L.; Lichtenberg, R. E.; Merrill, J. C.; Smart, J. Organomet. Chem. 1971, 27, 241.
54. Sheldrick, G. M. SHELXA 90: Program for absorption correction; University of Göttingen, Göttingen, Germany, 1990.
55. Sheldrick, G. M. SHELXTL-PC; Siemens Analytical X-ray Instruments Inc., Madison, WI, 1994.