Preparation, structure, and reactions of a lattice-framework disilene

Organometallics

Volumn 24, Issue 19, 2005, Pages 4629-4638

  Tsutsui, Shinobu ^a   Kwon, Eunsang ^a   Tanaka, Hiromasa ^a   Matsumoto, Shigeki ^a   Sakamoto, Kenkichi ^a,b  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; IRRADIATION; OXIDATION; PROBABILITY DENSITY FUNCTION; REACTION KINETICS;

DIHALOSILANES; METHOXYSILANE; THERMAL EQUILIBRIUM;

ORGANOMETALLICS;

EID: 25444483109     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om050362l     Document Type: Article

References (85)

1. West, R.; Fink, M. J.; Michl, J. Science 1981, 214, 1343.
2. For recent reviews on disilenes, see: (a) Iwamoto, T.; Kara, M. J. Synth. Org. Chem. 2004, 62, 94.
3. (b) Sekiguchi, A.; Lee, V. Ya. Chem. Rev. 2003, 103, 1429.
4. (c) Weidenbruch, M. J. Organomet. Chem. 2002, 646, 39.
5. (d) Weidenbruch, M. In The Chemistry of Organic Silicon Compounds III; Rappoport Z.; Apeloig, Y., Eds.; Wiley: Chichester, 2001; p 391.
6. (e) West, R. Polyhedron 2002, 21, 467.
7. (f) Kira, M.; Iwamoto, T. J. Organomet. Chem. 2000, 611, 236.
8. (g) Tokitoh, N.; Okazaki, R. Coord. Chem. Rev. 2000, 210, 251.
9. (h) Caspar, P. P.; West, R. In The Chemistry of Organic Silicon Compounds, 2nd ed.; Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons: New York, 1999; Part 3, p 2463.
10. (i) Okazaki, R.; West, R. Adv. Organomet. Chem. 1996, 39. 231.
11. (j) Weidenbruch, M. Coord. Chem. Rev. 1994, 130, 275.
12. (k) Grev. R. S. Adv. Organomet. Chem. 1991, 33, 125.
13. (l) Tsumuraya, T.; Batcheller, S. A.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1991, 30, 902.
14. (m) Raabe, G.; Michl, J. In The Chemistry of Organic Silicon Compounds, Part 2; Patai S., Rappoport, Z., Eds.; Wiley: New York, 1989; Chapter 17.
15. (n) West, R. Angew. Chem., Int. Ed. Engl. 1987, 26, 1201.
16. (o) Raabe, G.; Michl, J. Chem. Rev. 1985, 85, 5.
17. (p) West, R. Pure Appl. Chem. 1984, 56, 163.
18. Ishida, S.; Iwamoto, T.; Kabuto C.; Kira, M. Nature 2003, 421, 725.
19. (a) Sekiguchi, A.; Kinjo, R.; Ichinohe, M. Science 2004, 305, 1755.
20. (b) Wiberg, N.; Vasisht, S. K.; Fischer, G.; Mayer. P. Z. Anorg. Allg. Chem. 2004, 630, 1823.
21. Schmedake, T. A.; Haaf, M.; Apeloig, Y.; Müller, T.; Bukalov, S.; West, R. J. Am. Chem. Soc. 1999, 121, 9479.
22. Tokitoh, N.; Suzuki, H.; Okazaki, R.; Ogawa, K. J. Am. Chem. Soc. 1993, 115, 10428.
23. Suzuki, H.; Tokitoh, N.; Okazaki, R. Bull. Chem. Soc. Jpn. 1995, 68, 2471.
24. Tsutsui, S.; Sakamoto, K.; Kira, M. J. Am. Chem. Soc. 1998, 120, 9955.
25. (a) Masamune, S.; Eriyama, Y.; Kawase, T. Angew. Chem., Int. Ed. Engl. 1987, 26, 584.
26. (b) West, R.; Cavalieri, J. D.; Buffy, J. J.; Fry, C.; Zilm, K. W.; Duchamp, J. C.; Kira, M.; Iwamoto, T.; Müller, T.; Apeloig, Y. J. Am. Chem. Soc. 1997, 119, 4972.
27. For recent reviews on cyclopropenes, see: (a) Komatsu, K.; Kitagawa, T. Chem. Rev. 2003, 103, 1371.
28. (b) Billups, W. In The Chemistry of the Cydopropyl Group; Patai, S., Rappoport, A., Eds.; Wiley Interscience: New York, 1987.
29. (c) Komatsu, K.; Yoshida, Z. In Methods of Organic Chemistry (Houben-Weyl); de Meijere, A., Ed.; Thieme: Stuttgart, 1996; Vol. E17d, pp 3079-3192.
30. (a) Maier, G.; Neudert, J.; Wolf, O.; Pappusch, D.; Sekiguchi, A.; Tanaka, M.; Matsuo, T. J. Am, Chem. Soc: 2002, 124, 13819.
31. (b) Maier, G.; Kratt, A.; Schick, A.; Reisenauer, H. P.; Barbosa, F.; Gescheidt, G. Eur. J. Org. Chem. 2000, 1107.
32. (c) Maier, G.; Born, D.; Bauer, I.; Wolf, R.; Boese, R.; Cremer, D. Chem. Ber. 1994, 127, 173.
33. (a) Fink, M. J.; Puranik, D. B. Organometallics 1987, 6, 1809.
34. (b) Fink, M. J., Puranik, D. B.; Johnson, M. P. J. Am. Chem. Soc. 1988, 110, 1315.
35. (c) Puranik, D. B.; Fink, M. J. J. Am. Chem. Soc. 1989, 111, 5951.
36. (d) Puranik, D. B.; Johnson, M. P.; Fink, M. J. Organometallics 1989, 8, 770.
37. (e) Gee, J. R.; Howard. W. A.; McPherson, G. L.; Fink, M. J. J. Am. Chem. Soc. 1991, 113, 5461.
38. Schick, A. Doctral Dissertation, Universität Giessen, Germany, 1992.
39. Sakamoto, K.; Saeki, T.; Sakurai, H. Chem. Lett. 1993, 1675.
40. (a) Sakamoto, K.; Ogasawara, J.; Sakurai, H.; Kira, M. J. Am. Chem. Soc. 1997, 119, 3405.
41. (b) Veszpremi, T.; Takahashi, M.; Ogasawara, J.; Sakamoto, K.; Kira, M. J. Am. Chem. Soc. 1998, 120, 2408.
42. (c) Veszpremi, T.; Takahashi, M.; Hajgato, B.; Ogasawara, J.; Sakamoto, K.; Kira, M. J. Phys. Chem. (A) 1998, 102, 10530.
43. (d) Takahashi, M.; Sakamoto, K.; Kira, M. Int. J. Quantum Chem. 2001, 84, 198.
44. (e) Sakamoto, K.; Ogasawara, J.; Kon, Y.; Sunagawa, T.; Kira, M. Angew. Chem., Int. Ed. 2002, 41, 1402.
45. (f) Kon, Y.; Ogasawara, J.; Sakamoto, K.; Kabuto, C.; Kira, M. J. Am. Chem. Soc. 2003, 125, 9310.
46. (g) Kon, Y.; Sakamoto, K.; Kabuto, C.; Kira. M. Organometallics 2005, 24, 1407.
47. Matsumoto, S.; Tsutsui, S.; Kwon, E.; Sakamoto, K. Angew. Chem., Int. Ed. 2004, 43, 4610.
48. Tsutsui, S.; Tanaka, H.; Kwon, E.; Matsumotn, S.; Sakamoto, K. Organometallics 2004, 23, 5659.
49. Tanaka, H.; Kwon, E.; Tsutsui, S.; Mataumoto, S.; Sakamoto, K. Eur. J. Inorg. Chem. 2005, 1235.
50. (a) Ciabattoni, J.; Nathan, E. C.; Feiring, A. E.; Kocienski, P. J. Org. Synth. 1974, 54, 97.
51. (b) Ciabattoni, J.; Nathan, E. C.; Feiring, A. E.; Kocienski, P. J. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. 6, p 991.
52. (a) Conlin, R. T.; Zhang, S.; Namavari, M.; Bobbitt, K. L.; Fink, M. J. Organometallics 1989, 8, 571.
53. (b) Steinmetz, M. G.; Udayakumar, B. S.; Gordon, M. S. Organometallics 1989, 8, 530.
54. (a) Krogh-Jespersen, K. J. Phys. Chem. 1982, 56, 1492.
55. (b) Olbrich, G. Chem. Phys, Lett. 1986, 130, 115.
56. (c) Somasundram, K.; Amos, R. D.; Handy, N. C. Theor. Chim. Acta 1986, 70, 393.
57. (d) Teramae, H. J. Am. Chem. Soc. 1987, 109, 4140.
58. (e) Sari, L.; McCarthy, M. C.; Schaefer, H. F.; Thaddeus, P. J. Am. Chem. Soc. 2003, 125, 11409.
59. (a) Fink, M. J.; Michalczyk, M. J.; Haller, K. J.; West, R.; Michl, J. Organometallics 1984, 3, 793.
60. (b) Iwamoto, T.; Masuda, H.; Ishida, S.; Kabuto, C.; Kira, M. J. Am. Chem. Soc. 2003, 125, 9300.
61. (c) Suzuki, H,; Tokitoh, N.; Okazaki, R. Harada, J.; Ogawa, K.; Tomoda, S.; Goto, M. Organometallics 1998, 14, 1016.
62. Sekiguchi, A.; Maruki, I.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Chem. Soc., Chem. Commun. 1991, 341.
63. (a) Leites, L. A.; Bukalov, S. S.; Garbuzova, I. A.; West, R.; Mangette, J.; Spitzner, H. J. Organomet, Chem. 1997, 536-537, 425.
64. (b) Leites, L. A.; Bukalov, S. S.; Mangette, J. E.; Schmedake, T. A.; West, R. Mendeleev Commun. 1998, 2, 43.
65. The reaction of a cyclic silylene having an asymmetric chiral carbon with alcohols was reported. See: Sanji, T.; Fujiyama, H.; Yoshida, K.; Sakurai, H. J. Am. Chem. Soc. 2003, 125, 3216.
66. The preparation of an isolable dialkylsilylene was reported. See: Kira, M.; Ishida, S.; Iwamoto, T.; Kabuto, C. J. Am. Chem. Soc. 1999, 121, 9722.
67. Some 2,3-bis(trimethyl,silyl)-l-silacyclopropenes and a 2,3-diphenyl-1-ailacyclopropene were reported. See: (a) Tsutsui, S.; Sakamoto, K.; Kabuto, C.; Kira, M. Organometallics 1998, 17, 3819.
68. (b) Ichinohe, M.; Tanaka, T.; Sekiguchi, A. Chem. Lett. 2001, 1074.
69. (c) Ohshita, J.; Honda, N.; Nada, K.; Iida, T.; Mihara, T.; Matsuo, Y.; Kunai, A.; Naka, A.; Ishikawa, M. Organometallics 2003, 22, 2436.
70. Ishida, S.; Iwamnto, T. Kabuto, C.; Kira, M. Chem. Lett. 2001, 1102.
71. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, M. A.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, D. K.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andress, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian, Inc.: Pittsburgh, PA, 1998.
72. The computational method is based on a DFT calculation with Becke's three-parameter hybrid functional incorporating the Lee-Yang-Parr correlation functional (B3LYP). See: (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
73. (b) Lee, C.; Yang, W.; Parr, R. Phys. Rev. B 1988, 37, 785.
74. Cartesian coordinates of the disilenes studied in this study are presented in the Supporting Information.
75. Review: Apeloig, Y. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappopnrt, Z., Eds.: Wiley: Chichester. 1989; Chapter 2, p 129.
76. Karsten. K.-J. J. Am. Chem. Soc. 1985, 107, 537.
77. 17
78. (a) Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys. 1998, 109, 8218.
79. (b) Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454.
80. (c) Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, K. D. R. J. Chem. Phys. 1998, 108, 4439.
81. Wolinski, K.; Hilton. J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251.
82. SMART for Windows NT v5.054 Data Collection and SAINT+ for NT v5.00 Data Processing Software for the SMART system; Bruker Analytical X-ray Instruments, Inc.: Madison, WI, 1998.
83. SAINT Software Reference Manual, Version 4; Bruker Analytical X-ray Instruments, Inc.: Madison, WI, 1998.
84. Sheldrick, G. M. SADABS; Bruker Analytical X-ray Instruments, Inc.: Madison. WI, 1998.
85. Sheldrick, G. M. SHELXTL; Bruker Analytical X-ray Instruments. Inc.: Madison, WI, 1997.