1,1′-oligosilylferrocene compounds

Organometallics

Volumn 26, Issue 7, 2007, Pages 1762-1770

  Wagner, Harald ^a   Baumgartner, Judith ^a   Marschner, Christoph ^a  

^a GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULAR STRUCTURE; POTASSIUM COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

DIELECTROPHILES; FERROCENE;

ORGANOMETALLICS;

EID: 34047250650     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om061138e     Document Type: Article

References (70)

1. For a recent review on our polysilyl anion chemistry see: Marschner, C. Organometallics 2006, 25, 2110-2125.
2. For some excellent reviews on silyl anions see: (a) Lickiss, P. D.; Smith, C. M. Coord. Chem. Rev. 1995, 145, 75-124.
3. (b) Tamao, K.; Kawachi, A. Adv. Organomet. Chem. 1995, 38, 1-58.
4. (c) Belzner, J.; Dehnert J. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; J. Wiley & Sons: New York, 1998; Vol. 2, p 779.
5. (c) Sekiguchi, A.; Lee, V. Y.; Nanjo, M. Coord. Chem. Rev. 2000, 210, 11-45.
6. (d) Lerner, W. Coord. Chem. Rev. 2005, 249, 781-798.
7. (a) Marschner, C. Eur. J. Inorg. Chem. 1998, 221-226.
8. (b) Kayser, C.; Fischer, R.; Baumgartner, J.; Marschner, C. Organometallics 2002, 21, 1023-1030.
9. (a) Mechtler, C.; Marschner, C. Tetrahedron Lett. 1999, 40, 7777-7778.
10. (b) Kayser, C.; Kickelbick, G.; Marschner, C. Angew. Chem. 2002, 114, 1031-1034;
11. Angew. Chem., Int. Ed. 2002, 41, 989-992.
12. (c) Fischer, R.; Frank, D.; Gaderbauer, W.; Kayser, C.; Mechtler, C.; Baumgartner, J.; Marschner, C. Organometallics 2003, 22, 3723-3731.
13. (d) Fischer, R.; Konopa, T.; Baumgartner, J.; Marschner, C. Organometallics 2004, 23, 1899-1907.
14. For a compilation of recent work on silyldianions excluding the considerable number of silole dianions see the following: For 1,1-dianions: (a) Bravo-Zhivotovskii, D.; Molev, G.; Kravchenko, V.; Botoshansky, M.; Schmidt, A.; Apeloig, Y. Organometallics 2006, 25, 4719-4721.
15. (b) Bravo-Zhivotovskii, D.; Ruderfer, I.; Melamed, S.; Botoshansky, M.; Tumanskii, B.; Apeloig, Y. Angew. Chem., Int. Ed. 2005, 44, 739-743.
16. (c) Kira, M.; Iwamoto, T.; Yin, D.; Maruyama, T.; Sakurai, H. Chem. Lett. 2001, 910-911.
17. (d) Tokitoh, N.; Hatano, K.; Sadahiro, T.; Okazaki, R. Chem. Lett. 1999, 931-932.
18. (e) Sekiguchi, A; Ichinohe, M.; Yamaguchi, S. J. Am. Chem. Soc. 1999, 121, 10231-10232. For 1,2-dianions:
19. (f) Inoue, S.; Ichinohe, M.; Sekiguchi, A. Chem. Lett. 2005, 34, 1564-1565. For 1,4-dianions
20. (g) Apeloig, Y.; Korogodsky, G.; Bravo-Zhivotovskii, D.; Blaser, D.; Boese, R. Eur. J. Inorg. Chem. 2000, 1091-1095.
21. Rausch, M.; Vogel, M.; Rosenberg, H. J. Org. Chem. 1957, 22, 900-903.
22. (a) Kumada, M.; Mimura, K.; Ishikawa, M.; Shiina, K. Tetrahedron Lett. 1965, 6, 83-88.
23. (b) Kumada, M.; Kondo, T.; Mimura, K.; Ishikawa, M.; Yamamoto, K.; Ikeda, S.; Kondo, M. J. Organomet. Chem. 1972, 43, 293-305.
24. (a) Kondo, T.; Yamamoto, K.; Kumada, M. J. Organomet. Chem. 1972, 43, 315-321.
25. (b) Kumada, M.; Kondo, T.; Mimura, K.; Yamamoto, K.; Ishikawa, M. J. Organomet. Chem. 1972, 43, 307-314.
26. (a) Peckham, T. J.; Foucher, D. A.; Lough, A. J.; Manners, I. Can. J. Chem. 1995, 73, 2069-2078.
27. (b) Finckh, W.; Tang, B. Z.; Foucher, D. A.; Zamble, D. B.; Ziembinski, R.; Lough, A.; Manners, I. Organometallics 1993, 12, 823-829.
28. (c) Finckh, W.; Tang, B. Z.; Lough, A.; Manners, I. Organometallics 1992, 11, 2904-2911.
29. (a) Reddy, N. P.; Hayashi, T.; Tanaka, M. Chem. Commun. 1996, 1865-1866.
30. (b) Siemeling, U.; Krallmann, R.; Jutzi, P.; Neumann, B.; Stammler, H. G. Monatsh. Chem. 1994, 125, 579-586.
31. (a) Nguyen, M. T.; Diaz, A. F. Proc. Int. Soc. Opt. Eng. 1993, 1910, 230-240.
32. (b) Tanaka, M.; Hayashi, T. Bull. Chem. Soc. Jpn. 1993, 66, 334-336.
33. (a) Dement'ev, V. V.; Cervantes-Lee, F.; Parkanyi, L.; Sharma, H.; Pannell, K. H.; Nguyen, M. T.; Diaz, A. Organometallics 1993, 12, 1983-1987.
34. (b) Guerrero, A.; Gomez-Lara, J.; Cervantes, J.; Velasco, L.; Sharma, H.; Pannell, K. H. J. Organomet. Chem. 1992, 430, 273-286.
35. (c) Pannell, K. H.; Sharma, H. Organometallics 1991, 10, 954-949.
36. (d) Sharma, H. K.; Pannell, K. H.; Ledoux, I.; Zyss, J.; Ceccanti, A.; Zanello, P. Organometallics 2000, 19, 770-774.
37. (a) Jones, S. C.; Barlow, S.; O'Hare, D. Chem.-Eur. J. 2005, 11, 4473-4481.
38. (b) Tews, D.; Escarpa, Gaede, P. Organometallics 2004, 23, 968-975.
39. (a) Fallmann, H.; Fürpass, G.; Stüger, H.; Grogger, C. In Organosilicon Chemistry V: From Molecules to Materials; Auner, N., Weis, J., Eds.; Wiley-VCH: Weinheim, Germany, pp 490-494.
40. (b) Stüger, H.; Rautz, H.; Kickelbick, G.; Pietzsch, C. In Organosilicon Chemistry V: From Molecules to Materials; Auner, N., Weis, J., Eds.; Wiley-VCH: Weinheim, Germany, pp 462-466.
41. (c) Rautz, H.; Stüger, H.; Kickelbick, G.; Pietzsch, C. J. Organomet. Chem. 2001, 627, 167-178.
42. (d) Grogger, C.; Rautz, H.; Stüger, H. Monatsh. Chem. 2001, 132, 453-464.
43. (e) Grogger, C.; Siegl, H.; Rautz, H.; Stüger, H. In Organosilicon Chemistry IV: From Molecules to Materials; Auner, N.; Weis, J., Eds.; Wiley-VCH: Weinheim, Germany, pp 384-388.
44. (a) Palitzsch, W.; Roewer, G.; Pietzsch, C.; Jacob, K.; Merzweiler, K. In Organosilicon Chemistry IV: From Molecules to Materials; Auner, N., Weis, J., Eds.; Wiley-VCH: Weinheim, Germany, pp 300-305.
45. (b) Palitzsch, W.; Pietzsch, C.; Jacob, K.; Edelmann, F. T.; Gelbrich, T.; Lorenz, V.; Puttnat, M.; Roewer, G. J. Organomet. Chem. 1998, 554, 139-146.
46. Bochmann, M.; Green, M. L. H.; Powell, A. K.; Sassmannshausen, J.; Triller, M. U.; Wocadlo, S. J. Chem. Soc., Dalton Trans. 1999, 43-49.
47. Mechtler, C.; Zirngast, M.; Gaderbauer, W.; Wallner, A.; Baumgartner, J.; Marschner, C. J. Organomet. Chem. 2006, 697, 150-158.
48. Gilman, H.; Harrell, R. L., Jr. J. Organomet. Chem. 1967, 9, 67-76.
49. Fischer, R.; Konopa, T.; Ully, S.; Baumgartner, J.; Marschner, C. J. Organomet. Chem. 2003, 685, 79-92.
50. Markov, J.; Fischer, R.; Wagner, H.; Noormofidi, N.; Baumgartner, J.; Marschner, C. J. Chem. Soc., Dalton Trans. 2004, 2166-2169.
51. (a) Farwell, J. D.; Lappert, M. F.; Marschner, C.; Strissel, C.; Tilley, T. D. J. Organomet. Chem. 2000, 603, 185-188.
52. (b) Gaderbauer, W.; Zirngast, M.; Baumgartner, J.; Marschner, C.; Tilley, T. D. Organometallics 2006, 25, 2599-2606.
53. Arnold, J.; Tilley, T. D.; Rheingold, A. L.; Geib, S. J. Inorg. Chem. 1987, 26, 2106-2109.
54. Wagner, H.; Baumgartner, J.; Marschner, C. Organometallics 2005, 24, 4649-4653.
55. Sanganee, M.-J.; Steel, P. G.; Whelligan, D. K. J. Org. Chem. 2003, 68, 3337-3339.
56. Fischer, R.; Konopa, T.; Baumgartner, J.; Marschner, C. Organosilicon Chemistry VI; Auner, N., Weis, J., Eds.; Wiley-VCH: Weinheim, 2005; pp 314-318.
57. Chen, Y.-S.; Gaspar, P. P. Organometallics 1982, 1, 1410-1412.
58. Kayser, C.; Marschner, C. Monatsh. Chem. 1999, 130, 203-206.
59. Hirotsu, K.; Higuchi, T.; Shimada, A. Bull. Chem. Soc. Jpn. 1968, 41, 1557-1563.
60. For structurally characterized ferrocenes with tetramethyldisilanylene bridges see: (a) Wang, B.; Mu, Chen, D.; Xu, S.; Zhou, X. Organometallics 2004, 23, 6225-6230.
61. (b) Jutzi, P.; Krallmann, R.; Wolf, G.; Neumann, B.; Stammler, H.-G. Chem. Ber. 1991, 124, 2391-2399.
62. Fischer, R.; Konopa, T.; Ully, S.; Wallner, A.; Baumgartner, J.; Marschner, C. In Organosilicon Chemistry VI: From Molecules to Materials; Auner, N., Weis, J., Eds.; Wiley-VCH: Weinheim, 2005; pp 355-360.
63. (a) Morris, G. A.; Freeman, R. J. Am. Chem. Soc. 1979, 101, 760-762.
64. (b) Helmer, B. J.; West, R. Organometallics 1982, 1, 877-879.
65. Perich, J. W.; Johns, R. B. Synthesis 1988, 142-144.
66. Nützel, K. Houben-Weyl, Methoden d. Organic Chemistry; Müller, E., Ed.; Georg Thieme Verlag: Stuttgart, 1973; Vol. 13/2a, p 76.
67. Palitzsch, W.; Boehme, U.; Roewer, G. Chem. Commun. 1997, 803-804.
68. SAINTPLUS: Software Reference Manual, Version 6.45; Bruker-AXS: Madison-WI, 1997-2003.
69. Blessing, R. H. Acta Crystallogr. A 1995, 51, 33-38: SADABS: Version 2.1; Bruker: AXS, 1998.
70. Sheldrick, G. M. SHELX97, Programs for Crystal Structure Analysis (Release 97-2); Universität Göttingen: Göttingen, Germany, 1998.