The chemistry of stable silabenzenes

Journal of the Chinese Chemical Society

Volumn 55, Issue 3, 2008, Pages 487-507

  Tokitoh, Norihiro ^a   Wakita, Keiji ^b   Matsumoto, Takeshi ^a   Sasamori, Takahiro ^a   Okazaki, Renji ^b   Takagi, Nozomi ^c   Kimura, Masahiro ^c   Nagase, Shigeru ^c  

^a KYOTO UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

^c INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

Delocalized electrons; Kinetic stabilization; Silaaromatics; Silabenzene; Silabenzvalene

Indexed keywords

EID: 48349121726     PISSN: 00094536     EISSN: None     Source Type: Journal    
DOI: 10.1002/jccs.200800073     Document Type: Article

References (93)

1. Minkin, V. J.; Glukhovtsev, M. N.; Simkin, Y. B. Aromaticity and Antiaromaticity; Electronic and Structural Aspects; Wiley: New York, 1994.
2. For reviews on silaaromatic compounds, see: (a) Raabe, G.; Michl, J. Chem. Rev. 1985, 85, 419.
3. (b) Raabe, G.; Michl, J. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Ed.; Wiley: New York, 1989; pp 1102-1108.
4. (c) Apeloig Y. ibid., pp 151-166.
5. (d) Brook, A. G.; Brook, M. A. Adv. Organomet. Chem. 1996, 39, 71.
6. (e) Apeloig, Y.; Karni, M. In The Chemistry of Organic Silicon Compounds, Volume 2; Rappoport, Z.; Apeloig, Y.; Ed.; Wiley: New York, 1998; Chapter 1.
7. (a) Solouki, B.; Rosmus, P.; Bock, H.; Maier, G. Angew. Chem., Int. Ed. Engl. 1980, 19, 51.
8. (b) Maier, G.; Mihm, G.; Reisenauer, H. P. Angew. Chem., Int. Ed. Engl. 1980, 19, 52.
9. (c) Kreil, C. L.; Chapman, O. L.; Burns, G. T.; Barton, T. J. J. Am. Chem. Soc. 1980, 102, 841.
10. (d) Maier, G.; Mihm, G.; Reisenauer, H. P. Chem. Ber. 1982, 115, 801.
11. (e) Maier, G.; Mihm, G.; Baumgärtner, R. O. W.; Reisenauer, H. P. Chem. Ber. 1984, 117, 2337.
12. (f) Jutzi, P.; Meyer, M.; Reisenauer, H. P.; Maier, G. Chem. Ber. 1989, 122, 1227.
13. (a) Barton, T. J.; Banasiak, D. S. J. Am. Chem. Soc. 1977, 99, 5199.
14. (b) Barton, T. J.; Burns, G. T. J. Am. Chem. Soc. 1978, 100, 5246.
15. (c) Märkl, G.; Hofmeister, P. Angew. Chem., Int. Ed. Engl. 1979, 18, 789.
16. (d) Barton, T. J.; Vuper, M. J. Am. Chem. Soc. 1981, 103, 6788.
17. (e) Sekiguchi, A.; Tanikawa, H.; Ando, W. Organometallics, 1985, 4, 584.
18. (f) Märkl, G.; Schlosser, W. Angew. Chem. Int. Ed. Engl. 1988, 27, 963.
19. Recent reviews on low-coordinated organosilicon compounds: (a) Okazaki, R.; West, R. Adv. Organomet. Chem. 1996, 39, 232.
20. (b) Baines, K. M.; Stibbs, W. G. Adv. Organomet. Chem. 1996, 39, 275. For reviews of Si-C doubly bonded compounds, see ref. 1.
21. Astable tetrasila-1,3-butadiene has conjugated Si-Si double bonds. Weidenbruch, M.; Willms, S.; Saak, W.; Henkel, G. Angew. Chem. Int. Ed. Engl. 1997, 36, 2503.
22. Reports on the delocalization of silole anions and dianions: (a) Freeman, W. P.; Tilley, T. D.; Liable-Sands, L. M.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 10457.
23. (b) Goldfuss, B.; Schleyer, P. v. R. Hampel, F. Organometallics, 1996, 15, 1755.
24. (c) Goldfuss, B.; Schleyer, P. v. R. Organometallics, 1997, 16, 1543.
25. (d) Choi, S.-B.; Boudjouk, P.; Wei, P. J. Am. Chem. Soc. 1998, 120, 5814.
26. (e) Dysard, J. M.; Tilley, T. D. J. Am. Chem. Soc. 1998, 120, 8245.
27. (a) Arduengo, A. J., III; Bock, H.; Chen, H.; Denk, M.; Dixon, D. A.; Green, J. C.; Hermann, W. A.; Jones, N. L.; Wagner, M.; West, R. J. Am. Chem. Soc. 1994, 116, 6641.
28. (b) West, R.; Denk, M. Pure. Appl. Chem. 1996, 68, 785.
29. (c) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023.
30. (d) Boehme, C.; Frenking, G. J. Am. Chem. Soc. 1996, 118, 2039.
31. (e) West, R.; Buffy, J. J.; Haaf, M.; Müller, T.; Gehrhus, B.; Lappert, M. F.; Apeloig, Y. J. Am. Chem. Soc. 1998, 120, 1639.
32. Okazaki, R.; Tokitoh, N.; Matsumoto, T. In Synthetic Methods of Organometallic and Inorganic Chemistry; Herrmann, W. A.; Ed.; Thieme: New York, 1996; Vol. 2 (Auner, N., Klingebiel, U., Vol. Eds.), pp 260-269 references cited therein.
33. Examples for the applications of Tbt and Bbt groups: (a) Tokitoh, N.; Arai, Y.; Okazaki, R.; Nagase, S. Science 1997, 227, 78.
34. (b) Hatano, K.; Tokitoh, N.; Takagi, N.; Nagase, S. J. Am. Chem. Soc. 2000, 122, 4829.
35. (c) Tokitoh, N. J. Organomet. Chem. 2000, 611, 217.
36. (d) Okazaki, R.; Tokitoh, N. Acc. Chem. Res. 2000, 33, 625.
37. (e) Takeda, N.; Kajiwara, T.; Suzuki, H.; Okazaki, R.; Tokitoh, N. Chem. -Eur. J. 2003, 9, 3530.
38. (f) Sasamori, T.; Mieda, E.; Takeda, N.; Tokitoh, N. Angew. Chem. Int. Ed. 2005, 44, 3717.
39. (g) Sasamori, T.; Mieda, E.; Nagahora, N.; Sato, K.; Shiomi, D.; Takui, T.; Hosoi, Y.; Furukawa, Y.; Takagi, N.; Nagase, S.; Tokitoh, N. J. Am. Chem. Soc. 2006, 128, 12582.
40. (a) Wakita, K.; Tokitoh, N.; Okazaki, R.; Nagase, S. Angew. Chem. Int. Ed. 2000, 39, 634.
41. (b) Wakita, K.; Tokitoh, N.; Okazaki, R.; Takagi, N.; Nagase, S. J. Am. Chem. Soc. 2000, 122, 5648.
42. (a) Takeda, N.; Shinohara, A.; Tokitoh, N. Organometallics 2002, 21, 4024.
43. (b) Shinohara, A.; Takeda, N.; Sasamori, T.; Tokitoh, N. Bull. Chem. Soc. Jpn. 2005, 78, 977.
44. (a) Tokitoh, N.; Wakita, K.; Okazaki, R.; Nagase, S.; Schleyer, P. v. R.; Jiao, H. J. Am. Chem. Soc. 1997, 119, 6951.
45. (b) Wakita, K.; Tokitoh, N.; Okazaki, R.; Nagase, S.; Schleyer, P. v. R.; Jiao, H. J. Am. Chem. Soc. 1999, 121, 11336.
46. (c) Wakita, K.; Tokitoh, N.; Okazaki, R. Bull. Chem. Soc. Jpn. 2000, 73, 2157.
47. (a) Takeda, N.; Shinohara, A.; Tokitoh, N. Organometallics 2002, 21, 256.
48. (b) Shinohara, A.; Takeda, N.; Tokitoh, N. J. Am. Chem. Soc. 2003, 125, 10804.
49. Tokitoh, N.; Shinohara, A.; Matsumoto, T.; Sasamori, T.; Takeda, N.; Furukawa, Y. Organometallics, in press.
50. (a) Nakata, N.; Takeda, N.; Tokitoh, N. Organometallics 2001, 20, 5507.
51. (b) Nakata, N.; Takeda, N.; Tokitoh, N. J. Am. Chem. Soc. 2002, 124, 6914.
52. (c) Nakata, N.; Takeda, N.; Tokitoh, N. Chem. Lett. 2002, 818.
53. (d) Nakata, N.; Takeda, N.; Tokitoh, N. Angew. Chem. Int. Ed. 2003, 42, 115.
54. (e) Nakata, N.; Takeda, N.; Tokitoh, N. Organometallics 2003, 22, 481.
55. (f) Nakata, N.; Takeda, N.; Tokitoh, N. J. Organomet. Chem. 2003, 672, 66.
56. (g) Sasamori, T.; Inamura, K.; Hoshino, W.; Nakata, N.; Mizuhata, Y.; Watanabe, Y.; Furukawa, Y.; Tokitoh, N. Organometallics 2006, 25, 3533.
57. Mizuhata, Y.; Sasamori, T.; Takeda, N.; Tokitoh, N. J. Am. Chem. Soc. 2006, 128, 1050.
58. Bbt group has almost the same steric protection ability as that of Tbt group, but sometimes shows different chemical or crystallographic behavior. For example, see: (a) Kano, N.; Tokitoh, N.; Okazaki, R. Organometallics 1998, 17, 1241.
59. (b) Tokitoh, N.; Sasamori, T.; Okazaki, R. Chem. Lett. 1998, 725.
60. (c) Sasamori, T.; Takeda, N.; Tokitoh, N. J. Phys. Org. Chem. 2003, 16, 450.
61. (d) Sasamori, T.; Arai, Y.; Takeda, N.; Okazaki, R.; Furukawa, Y.; Kimura, M.; Nagase, S.; Tokitoh, N. Bull. Chem. Soc. Jpn. 2002, 75, 661.
62. Wakita, K.; Tokitoh, N.; Okazaki, R. Chem. Lett. 1998, 687.
63. Märkl, G.; Baier, H.; Hofmeister, P.; Kess, F.; Soper, U. J. Organomet. Chem. 1979, 173, 125.
64. 6.
65. Delpon-Lacaz, G.; Couret, G. J. Organomet. Chem. 1994, 480, C14.
66. Kalinowski, H-O.; Berger, S.; Braun, S. Carbon-13 NMR Spectroscopy translated by J. K. Becconsall; Wiley: New York, 1986; p 600.
67. Brook, A. G.; Abdesaken, F.; Gutekunst, G.; Plavac, N. Organometallics 1982, 1, 994.
68. Brook, A. G.; Nyburg, S. C.; Abdesaken, F.; Gutekunst, B.; Gutekunst, G.; Kallury, R. K. M. R.; Poon, Y. C.; Chang, Y.; Wong-Ng, W. J. Am. Chem. Soc. 1982, 104, 5668.
69. (a) Wiberg, N.; Wagner, G.; Müller, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 229.
70. (b) Gutowsky, H. S.; Chen, J.; Hajduk, P. J.; Keen, J. D.; Chuang, C.; Emilsson, T. J. Am. Chem. Soc. 1991, 113, 4747.
71. Sheldrick, W. M. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Ed.; Wiley: New York, 1989; p 246.
72. Maier, G.; Schöttler, Reisenauer, H. P. Tetrahedron Lett. 1985, 26, 4079.
73. Previous calculations indicated that dimerization of silabenzene is exothermic by ΔH = -21.5 kcal/mol. Brown, E. C.; Borden, W. T. Organometallics 2000, 19, 2208.
74. The structural difference between Tbt and Bbt groups was revealed by X-ray analysis of TbtBr and BbtBr. Sasamori, T. Dissertation, Kyushu Univ., 2002.
75. It was found that the dimerization reaction pathway was followed by the rotation processes of Tbt and Bbt groups for dimers 19a,b leading to the formation of the more stable geometries. Since the rotation barrier of the Tbt and Bbt group of 19a,b should be smaller than the activation energies of the dimerization of silabenzenes 1a,b, the rotational processes leading to the more stable geometries were not discussed here.
76. 4. Horspool, W. M. In Synthetic Organic Photochemistry; Horspool, W. M.; Ed.; Plenum Press: New York, 1984; p 493.
77. Williams, E. A. In The Chemistry of Organic Silicon Compounds; Patai, S.; Rappoport, Z.; Ed.; Wiley: New York, 1989; p 536.
78. Since prolonged irradiation afforded polymeric products, the possibility of the formation of unstable isomers cannot be completely excluded.
79. (a) Ando, W.; Shiba, T.; Hidaka, T.; Morihashi, K.; Kikuchi, O. J. Am. Chem. Soc. 1997, 119, 3629.
80. (b) Kabe, Y.; Ohkubo, K.; Ishikawa, H.; Ando, W. J. Am. Chem. Soc. 2000, 122, 3775.
81. Chandrasekhar, J.; Schleyer, P. v. R.; Baumgartner, R. O. W.; Reetz, M. T. J. Org. Chem. 1983, 48, 3453.
82. (a) Kiprof, P.; Brown, A. B. Internet J. Chem. 1999, 2, 23.
83. (b) Dhevi, D. M.; Priyakumar, U. D.; Sastry, G. N. J. Mol. Struct. (Theochem) 2002, 618, 173.
84. (c) Priyakumar, U. D.; Dinadayalane, T. C.; Sastry, G. N. New J. Chem. 2002, 26, 347.
85. (d) Priyakumar, U. D.; Saravanan, D.; Sastry, G. N. Organometallics 2002, 21, 4823.
86. (e) Priyakumar, U. D.; Sastry, G. N. Organometallics 2002, 21, 1493.
87. (f) Priyakumar, U. D.; Punnagai, M.; Sastry, G. N. J. Organomet. Chem. 2004, 689, 1284.
88. Unno, M. Dissertation, The University of Tokyo, 1988.
89. Ashe III, A. J.; Chan, W.-T. J. Org. Chem. 1979, 44, 1409.
90. Suzuki, H.; Tokitoh, N.; Okazaki, R.; Harada, J.; Ogawa, K.; Tomoda, S.; Goto, M. Organometallics 1995, 14, 1016.
91. Calculations were carried out using the Gaussian 98 program. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, Jr., 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, A. D.; 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.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian, Inc.: Pittsburgh, PA, 1998.
92. Higashi, T. ABSCOR: Program for Absorption Correction; Rigaku Corporation, 1995.
93. Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.