Aromatic β-silylethenylation reactions via organogallium compounds

Bulletin of the Chemical Society of Japan

Volumn 72, Issue 7, 1999, Pages 1445-1458

  Kido, Yoshiyuki ^a   Yoshimura, Satoru ^a   Yamaguchi, Masahiko ^a   Uchimaru, Tadafumi ^b  

^a TOHOKU UNIVERSITY   (Japan)

^b NATL INST OF MAT AND CHEM RES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; BENZENE DERIVATIVE; GALLIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0032765847     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.72.1445     Document Type: Article

References (82)

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17. For examples: K. Y. Yuldashev and I. P. Tsukervanik, J. Gen. Chem. USSR, 34, 2668 (1964); R. M. Roberts and M. B. Abdel-Baset, J. Org. Chem., 41, 1698 (1976); A. A. Schegolev, W. A. Smit, S. A. Khurshudyan, V. A. Chertkov, and V. F. Kucherov, Synthesis, 1977, 324; P. J. Stang and A. G. Anderson, J. Am. Chem. Soc., 100, 1520 (1978); J. Hrabovsk'y and J. Kovác, Collect. Czech. Chem. Commun., 44, 2096 (1979); V. D. Ryabov and V. Y. Korobkov, J. Org. Chem. USSR, 16, 337 (1980); R.-L. Fan, J. I. Dickstein, and S. I. Miller, J. Org. Chem., 47, 2466 (1982); T. Kitamura, S. Kobayashi, H. Taniguchi, and Z. Rappoport, J. Org. Chem., 47, 5003 (1982); M. Ochiai, Y. Takaoka, K. Sumi, and Y. Nagao, J Chem. Soc., Chem. Commun., 1986, 1382; T. Kitamura, I. Nakamura, T. Kabashima, S. Kobayashi, and H. Taniguchi, J. Am. Chem. Soc., 112, 6149 (1990); T. Takeda, F. Kanamori, H. Matsusita, and T. Fujiwara, Tetrahedron Lett., 32, 6563 (1991); G. Sartori, F. Bigi, A. Pastorio, C. Porta, A. Arienti, R. Maggi, N. Moretti, and G. Gnappi, Tetrahedron Lett., 36, 9177 (1995).
18. For examples: K. Y. Yuldashev and I. P. Tsukervanik, J. Gen. Chem. USSR, 34, 2668 (1964); R. M. Roberts and M. B. Abdel-Baset, J. Org. Chem., 41, 1698 (1976); A. A. Schegolev, W. A. Smit, S. A. Khurshudyan, V. A. Chertkov, and V. F. Kucherov, Synthesis, 1977, 324; P. J. Stang and A. G. Anderson, J. Am. Chem. Soc., 100, 1520 (1978); J. Hrabovsk'y and J. Kovác, Collect. Czech. Chem. Commun., 44, 2096 (1979); V. D. Ryabov and V. Y. Korobkov, J. Org. Chem. USSR, 16, 337 (1980); R.-L. Fan, J. I. Dickstein, and S. I. Miller, J. Org. Chem., 47, 2466 (1982); T. Kitamura, S. Kobayashi, H. Taniguchi, and Z. Rappoport, J. Org. Chem., 47, 5003 (1982); M. Ochiai, Y. Takaoka, K. Sumi, and Y. Nagao, J Chem. Soc., Chem. Commun., 1986, 1382; T. Kitamura, I. Nakamura, T. Kabashima, S. Kobayashi, and H. Taniguchi, J. Am. Chem. Soc., 112, 6149 (1990); T. Takeda, F. Kanamori, H. Matsusita, and T. Fujiwara, Tetrahedron Lett., 32, 6563 (1991); G. Sartori, F. Bigi, A. Pastorio, C. Porta, A. Arienti, R. Maggi, N. Moretti, and G. Gnappi, Tetrahedron Lett., 36, 9177 (1995).
19. For examples: K. Y. Yuldashev and I. P. Tsukervanik, J. Gen. Chem. USSR, 34, 2668 (1964); R. M. Roberts and M. B. Abdel-Baset, J. Org. Chem., 41, 1698 (1976); A. A. Schegolev, W. A. Smit, S. A. Khurshudyan, V. A. Chertkov, and V. F. Kucherov, Synthesis, 1977, 324; P. J. Stang and A. G. Anderson, J. Am. Chem. Soc., 100, 1520 (1978); J. Hrabovsk'y and J. Kovác, Collect. Czech. Chem. Commun., 44, 2096 (1979); V. D. Ryabov and V. Y. Korobkov, J. Org. Chem. USSR, 16, 337 (1980); R.-L. Fan, J. I. Dickstein, and S. I. Miller, J. Org. Chem., 47, 2466 (1982); T. Kitamura, S. Kobayashi, H. Taniguchi, and Z. Rappoport, J. Org. Chem., 47, 5003 (1982); M. Ochiai, Y. Takaoka, K. Sumi, and Y. Nagao, J Chem. Soc., Chem. Commun., 1986, 1382; T. Kitamura, I. Nakamura, T. Kabashima, S. Kobayashi, and H. Taniguchi, J. Am. Chem. Soc., 112, 6149 (1990); T. Takeda, F. Kanamori, H. Matsusita, and T. Fujiwara, Tetrahedron Lett., 32, 6563 (1991); G. Sartori, F. Bigi, A. Pastorio, C. Porta, A. Arienti, R. Maggi, N. Moretti, and G. Gnappi, Tetrahedron Lett., 36, 9177 (1995).
20. For examples: K. Y. Yuldashev and I. P. Tsukervanik, J. Gen. Chem. USSR, 34, 2668 (1964); R. M. Roberts and M. B. Abdel-Baset, J. Org. Chem., 41, 1698 (1976); A. A. Schegolev, W. A. Smit, S. A. Khurshudyan, V. A. Chertkov, and V. F. Kucherov, Synthesis, 1977, 324; P. J. Stang and A. G. Anderson, J. Am. Chem. Soc., 100, 1520 (1978); J. Hrabovsk'y and J. Kovác, Collect. Czech. Chem. Commun., 44, 2096 (1979); V. D. Ryabov and V. Y. Korobkov, J. Org. Chem. USSR, 16, 337 (1980); R.-L. Fan, J. I. Dickstein, and S. I. Miller, J. Org. Chem., 47, 2466 (1982); T. Kitamura, S. Kobayashi, H. Taniguchi, and Z. Rappoport, J. Org. Chem., 47, 5003 (1982); M. Ochiai, Y. Takaoka, K. Sumi, and Y. Nagao, J Chem. Soc., Chem. Commun., 1986, 1382; T. Kitamura, I. Nakamura, T. Kabashima, S. Kobayashi, and H. Taniguchi, J. Am. Chem. Soc., 112, 6149 (1990); T. Takeda, F. Kanamori, H. Matsusita, and T. Fujiwara, Tetrahedron Lett., 32, 6563 (1991); G. Sartori, F. Bigi, A. Pastorio, C. Porta, A. Arienti, R. Maggi, N. Moretti, and G. Gnappi, Tetrahedron Lett., 36, 9177 (1995).
21. For examples: K. Y. Yuldashev and I. P. Tsukervanik, J. Gen. Chem. USSR, 34, 2668 (1964); R. M. Roberts and M. B. Abdel-Baset, J. Org. Chem., 41, 1698 (1976); A. A. Schegolev, W. A. Smit, S. A. Khurshudyan, V. A. Chertkov, and V. F. Kucherov, Synthesis, 1977, 324; P. J. Stang and A. G. Anderson, J. Am. Chem. Soc., 100, 1520 (1978); J. Hrabovsk'y and J. Kovác, Collect. Czech. Chem. Commun., 44, 2096 (1979); V. D. Ryabov and V. Y. Korobkov, J. Org. Chem. USSR, 16, 337 (1980); R.-L. Fan, J. I. Dickstein, and S. I. Miller, J. Org. Chem., 47, 2466 (1982); T. Kitamura, S. Kobayashi, H. Taniguchi, and Z. Rappoport, J. Org. Chem., 47, 5003 (1982); M. Ochiai, Y. Takaoka, K. Sumi, and Y. Nagao, J Chem. Soc., Chem. Commun., 1986, 1382; T. Kitamura, I. Nakamura, T. Kabashima, S. Kobayashi, and H. Taniguchi, J. Am. Chem. Soc., 112, 6149 (1990); T. Takeda, F. Kanamori, H. Matsusita, and T. Fujiwara, Tetrahedron Lett., 32, 6563 (1991); G. Sartori, F. Bigi, A. Pastorio, C. Porta, A. Arienti, R. Maggi, N. Moretti, and G. Gnappi, Tetrahedron Lett., 36, 9177 (1995).
22. For examples: K. Y. Yuldashev and I. P. Tsukervanik, J. Gen. Chem. USSR, 34, 2668 (1964); R. M. Roberts and M. B. Abdel-Baset, J. Org. Chem., 41, 1698 (1976); A. A. Schegolev, W. A. Smit, S. A. Khurshudyan, V. A. Chertkov, and V. F. Kucherov, Synthesis, 1977, 324; P. J. Stang and A. G. Anderson, J. Am. Chem. Soc., 100, 1520 (1978); J. Hrabovsk'y and J. Kovác, Collect. Czech. Chem. Commun., 44, 2096 (1979); V. D. Ryabov and V. Y. Korobkov, J. Org. Chem. USSR, 16, 337 (1980); R.-L. Fan, J. I. Dickstein, and S. I. Miller, J. Org. Chem., 47, 2466 (1982); T. Kitamura, S. Kobayashi, H. Taniguchi, and Z. Rappoport, J. Org. Chem., 47, 5003 (1982); M. Ochiai, Y. Takaoka, K. Sumi, and Y. Nagao, J Chem. Soc., Chem. Commun., 1986, 1382; T. Kitamura, I. Nakamura, T. Kabashima, S. Kobayashi, and H. Taniguchi, J. Am. Chem. Soc., 112, 6149 (1990); T. Takeda, F. Kanamori, H. Matsusita, and T. Fujiwara, Tetrahedron Lett., 32, 6563 (1991); G. Sartori, F. Bigi, A. Pastorio, C. Porta, A. Arienti, R. Maggi, N. Moretti, and G. Gnappi, Tetrahedron Lett., 36, 9177 (1995).
23. For examples: K. Y. Yuldashev and I. P. Tsukervanik, J. Gen. Chem. USSR, 34, 2668 (1964); R. M. Roberts and M. B. Abdel-Baset, J. Org. Chem., 41, 1698 (1976); A. A. Schegolev, W. A. Smit, S. A. Khurshudyan, V. A. Chertkov, and V. F. Kucherov, Synthesis, 1977, 324; P. J. Stang and A. G. Anderson, J. Am. Chem. Soc., 100, 1520 (1978); J. Hrabovsk'y and J. Kovác, Collect. Czech. Chem. Commun., 44, 2096 (1979); V. D. Ryabov and V. Y. Korobkov, J. Org. Chem. USSR, 16, 337 (1980); R.-L. Fan, J. I. Dickstein, and S. I. Miller, J. Org. Chem., 47, 2466 (1982); T. Kitamura, S. Kobayashi, H. Taniguchi, and Z. Rappoport, J. Org. Chem., 47, 5003 (1982); M. Ochiai, Y. Takaoka, K. Sumi, and Y. Nagao, J Chem. Soc., Chem. Commun., 1986, 1382; T. Kitamura, I. Nakamura, T. Kabashima, S. Kobayashi, and H. Taniguchi, J. Am. Chem. Soc., 112, 6149 (1990); T. Takeda, F. Kanamori, H. Matsusita, and T. Fujiwara, Tetrahedron Lett., 32, 6563 (1991); G. Sartori, F. Bigi, A. Pastorio, C. Porta, A. Arienti, R. Maggi, N. Moretti, and G. Gnappi, Tetrahedron Lett., 36, 9177 (1995).
24. For examples: K. Y. Yuldashev and I. P. Tsukervanik, J. Gen. Chem. USSR, 34, 2668 (1964); R. M. Roberts and M. B. Abdel-Baset, J. Org. Chem., 41, 1698 (1976); A. A. Schegolev, W. A. Smit, S. A. Khurshudyan, V. A. Chertkov, and V. F. Kucherov, Synthesis, 1977, 324; P. J. Stang and A. G. Anderson, J. Am. Chem. Soc., 100, 1520 (1978); J. Hrabovsk'y and J. Kovác, Collect. Czech. Chem. Commun., 44, 2096 (1979); V. D. Ryabov and V. Y. Korobkov, J. Org. Chem. USSR, 16, 337 (1980); R.-L. Fan, J. I. Dickstein, and S. I. Miller, J. Org. Chem., 47, 2466 (1982); T. Kitamura, S. Kobayashi, H. Taniguchi, and Z. Rappoport, J. Org. Chem., 47, 5003 (1982); M. Ochiai, Y. Takaoka, K. Sumi, and Y. Nagao, J Chem. Soc., Chem. Commun., 1986, 1382; T. Kitamura, I. Nakamura, T. Kabashima, S. Kobayashi, and H. Taniguchi, J. Am. Chem. Soc., 112, 6149 (1990); T. Takeda, F. Kanamori, H. Matsusita, and T. Fujiwara, Tetrahedron Lett., 32, 6563 (1991); G. Sartori, F. Bigi, A. Pastorio, C. Porta, A. Arienti, R. Maggi, N. Moretti, and G. Gnappi, Tetrahedron Lett., 36, 9177 (1995).
25. For examples: K. Y. Yuldashev and I. P. Tsukervanik, J. Gen. Chem. USSR, 34, 2668 (1964); R. M. Roberts and M. B. Abdel-Baset, J. Org. Chem., 41, 1698 (1976); A. A. Schegolev, W. A. Smit, S. A. Khurshudyan, V. A. Chertkov, and V. F. Kucherov, Synthesis, 1977, 324; P. J. Stang and A. G. Anderson, J. Am. Chem. Soc., 100, 1520 (1978); J. Hrabovsk'y and J. Kovác, Collect. Czech. Chem. Commun., 44, 2096 (1979); V. D. Ryabov and V. Y. Korobkov, J. Org. Chem. USSR, 16, 337 (1980); R.-L. Fan, J. I. Dickstein, and S. I. Miller, J. Org. Chem., 47, 2466 (1982); T. Kitamura, S. Kobayashi, H. Taniguchi, and Z. Rappoport, J. Org. Chem., 47, 5003 (1982); M. Ochiai, Y. Takaoka, K. Sumi, and Y. Nagao, J Chem. Soc., Chem. Commun., 1986, 1382; T. Kitamura, I. Nakamura, T. Kabashima, S. Kobayashi, and H. Taniguchi, J. Am. Chem. Soc., 112, 6149 (1990); T. Takeda, F. Kanamori, H. Matsusita, and T. Fujiwara, Tetrahedron Lett., 32, 6563 (1991); G. Sartori, F. Bigi, A. Pastorio, C. Porta, A. Arienti, R. Maggi, N. Moretti, and G. Gnappi, Tetrahedron Lett., 36, 9177 (1995).
26. For examples: K. Y. Yuldashev and I. P. Tsukervanik, J. Gen. Chem. USSR, 34, 2668 (1964); R. M. Roberts and M. B. Abdel-Baset, J. Org. Chem., 41, 1698 (1976); A. A. Schegolev, W. A. Smit, S. A. Khurshudyan, V. A. Chertkov, and V. F. Kucherov, Synthesis, 1977, 324; P. J. Stang and A. G. Anderson, J. Am. Chem. Soc., 100, 1520 (1978); J. Hrabovsk'y and J. Kovác, Collect. Czech. Chem. Commun., 44, 2096 (1979); V. D. Ryabov and V. Y. Korobkov, J. Org. Chem. USSR, 16, 337 (1980); R.-L. Fan, J. I. Dickstein, and S. I. Miller, J. Org. Chem., 47, 2466 (1982); T. Kitamura, S. Kobayashi, H. Taniguchi, and Z. Rappoport, J. Org. Chem., 47, 5003 (1982); M. Ochiai, Y. Takaoka, K. Sumi, and Y. Nagao, J Chem. Soc., Chem. Commun., 1986, 1382; T. Kitamura, I. Nakamura, T. Kabashima, S. Kobayashi, and H. Taniguchi, J. Am. Chem. Soc., 112, 6149 (1990); T. Takeda, F. Kanamori, H. Matsusita, and T. Fujiwara, Tetrahedron Lett., 32, 6563 (1991); G. Sartori, F. Bigi, A. Pastorio, C. Porta, A. Arienti, R. Maggi, N. Moretti, and G. Gnappi, Tetrahedron Lett., 36, 9177 (1995).
27. For examples: K. Y. Yuldashev and I. P. Tsukervanik, J. Gen. Chem. USSR, 34, 2668 (1964); R. M. Roberts and M. B. Abdel-Baset, J. Org. Chem., 41, 1698 (1976); A. A. Schegolev, W. A. Smit, S. A. Khurshudyan, V. A. Chertkov, and V. F. Kucherov, Synthesis, 1977, 324; P. J. Stang and A. G. Anderson, J. Am. Chem. Soc., 100, 1520 (1978); J. Hrabovsk'y and J. Kovác, Collect. Czech. Chem. Commun., 44, 2096 (1979); V. D. Ryabov and V. Y. Korobkov, J. Org. Chem. USSR, 16, 337 (1980); R.-L. Fan, J. I. Dickstein, and S. I. Miller, J. Org. Chem., 47, 2466 (1982); T. Kitamura, S. Kobayashi, H. Taniguchi, and Z. Rappoport, J. Org. Chem., 47, 5003 (1982); M. Ochiai, Y. Takaoka, K. Sumi, and Y. Nagao, J Chem. Soc., Chem. Commun., 1986, 1382; T. Kitamura, I. Nakamura, T. Kabashima, S. Kobayashi, and H. Taniguchi, J. Am. Chem. Soc., 112, 6149 (1990); T. Takeda, F. Kanamori, H. Matsusita, and T. Fujiwara, Tetrahedron Lett., 32, 6563 (1991); G. Sartori, F. Bigi, A. Pastorio, C. Porta, A. Arienti, R. Maggi, N. Moretti, and G. Gnappi, Tetrahedron Lett., 36, 9177 (1995).
28. Examples of organometallic alkenylation of aromatic hydrocarbon: I. Moritani and Y. Fujiwara, Synthesis, 1973, 524; Y. Tokunaga, T. Sakakura, andM.Tanaka, J. Mol. Cat., 56, 305 (1989); W. T. Boese and A. S. Goldman, Organometallics, 10, 782 (1991).
29. Examples of organometallic alkenylation of aromatic hydrocarbon: I. Moritani and Y. Fujiwara, Synthesis, 1973, 524; Y. Tokunaga, T. Sakakura, andM.Tanaka, J. Mol. Cat., 56, 305 (1989); W. T. Boese and A. S. Goldman, Organometallics, 10, 782 (1991).
30. Examples of organometallic alkenylation of aromatic hydrocarbon: I. Moritani and Y. Fujiwara, Synthesis, 1973, 524; Y. Tokunaga, T. Sakakura, andM.Tanaka, J. Mol. Cat., 56, 305 (1989); W. T. Boese and A. S. Goldman, Organometallics, 10, 782 (1991).
31. For recent examples: S. Kobayashi, K. Koide, and M. Ohno, Tetrahedron Lett., 31, 2435 (1990); Y. Fukuda, S. Matsubara, C. Lambert, H. Shiragami, T. Nanko, K. Utimoto, and H. Nozaki, Bull. Chem. Soc. Jpn., 64, 1810 (1991); Y. Hashimoto, K. Hirata, H. Kagoshima, N. Kihara, M. Hasegawa, and K. Saigo, Tetrahedron, 49, 5969 (1993); M. Shibasaki, H. Sasai, and T. Arai, Angew. Chem., Int. Ed. Engl., 36, 1236 (1997); Y. Han and Y.-Z. Huang, Tetrahedron Lett., 39, 7751 (1998).
32. For recent examples: S. Kobayashi, K. Koide, and M. Ohno, Tetrahedron Lett., 31, 2435 (1990); Y. Fukuda, S. Matsubara, C. Lambert, H. Shiragami, T. Nanko, K. Utimoto, and H. Nozaki, Bull. Chem. Soc. Jpn., 64, 1810 (1991); Y. Hashimoto, K. Hirata, H. Kagoshima, N. Kihara, M. Hasegawa, and K. Saigo, Tetrahedron, 49, 5969 (1993); M. Shibasaki, H. Sasai, and T. Arai, Angew. Chem., Int. Ed. Engl., 36, 1236 (1997); Y. Han and Y.-Z. Huang, Tetrahedron Lett., 39, 7751 (1998).
33. For recent examples: S. Kobayashi, K. Koide, and M. Ohno, Tetrahedron Lett., 31, 2435 (1990); Y. Fukuda, S. Matsubara, C. Lambert, H. Shiragami, T. Nanko, K. Utimoto, and H. Nozaki, Bull. Chem. Soc. Jpn., 64, 1810 (1991); Y. Hashimoto, K. Hirata, H. Kagoshima, N. Kihara, M. Hasegawa, and K. Saigo, Tetrahedron, 49, 5969 (1993); M. Shibasaki, H. Sasai, and T. Arai, Angew. Chem., Int. Ed. Engl., 36, 1236 (1997); Y. Han and Y.-Z. Huang, Tetrahedron Lett., 39, 7751 (1998).
34. For recent examples: S. Kobayashi, K. Koide, and M. Ohno, Tetrahedron Lett., 31, 2435 (1990); Y. Fukuda, S. Matsubara, C. Lambert, H. Shiragami, T. Nanko, K. Utimoto, and H. Nozaki, Bull. Chem. Soc. Jpn., 64, 1810 (1991); Y. Hashimoto, K. Hirata, H. Kagoshima, N. Kihara, M. Hasegawa, and K. Saigo, Tetrahedron, 49, 5969 (1993); M. Shibasaki, H. Sasai, and T. Arai, Angew. Chem., Int. Ed. Engl., 36, 1236 (1997); Y. Han and Y.-Z. Huang, Tetrahedron Lett., 39, 7751 (1998).
35. For recent examples: S. Kobayashi, K. Koide, and M. Ohno, Tetrahedron Lett., 31, 2435 (1990); Y. Fukuda, S. Matsubara, C. Lambert, H. Shiragami, T. Nanko, K. Utimoto, and H. Nozaki, Bull. Chem. Soc. Jpn., 64, 1810 (1991); Y. Hashimoto, K. Hirata, H. Kagoshima, N. Kihara, M. Hasegawa, and K. Saigo, Tetrahedron, 49, 5969 (1993); M. Shibasaki, H. Sasai, and T. Arai, Angew. Chem., Int. Ed. Engl., 36, 1236 (1997); Y. Han and Y.-Z. Huang, Tetrahedron Lett., 39, 7751 (1998).
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60. Silicon stabilized vinyl cations were trapped by solvent: L. G. Kozar, R. D. Clark, and C. H. Heathcock, J. Org. Chem., 42, 1386 (1977); W. S. Johnson, T. M. Yarnell, R. F. Myers, D. R. Morton, and S. G. Boots, J. Org. Chem., 45, 1254 (1980).
61. Discussions on the open and bridged vinyl cation: G. A. Olah and R. J. Spear, J. Am. Chem. Soc., 97, 1845 (1975); F. Marcuzzi, G. Melloni, and G. Modena, / Org. Chem., 44, 3022 (1979); K. Yates and T. A. Go, J. Org. Chem., 45, 2377 and 2385 (1980), and references cited therein.
62. Discussions on the open and bridged vinyl cation: G. A. Olah and R. J. Spear, J. Am. Chem. Soc., 97, 1845 (1975); F. Marcuzzi, G. Melloni, and G. Modena, / Org. Chem., 44, 3022 (1979); K. Yates and T. A. Go, J. Org. Chem., 45, 2377 and 2385 (1980), and references cited therein.
63. Discussions on the open and bridged vinyl cation: G. A. Olah and R. J. Spear, J. Am. Chem. Soc., 97, 1845 (1975); F. Marcuzzi, G. Melloni, and G. Modena, / Org. Chem., 44, 3022 (1979); K. Yates and T. A. Go, J. Org. Chem., 45, 2377 and 2385 (1980), and references cited therein.
64. For recent examples: H.-U. Siehl, F.-P. Kaufmann, Y. Apelog, V. Braude, D. Danovish, A. Berndt, and N. Stamatis, Angew. Chem., Int. Ed. Engl., 31, 1479 (1991); H.-U. Siehl and F.-P. Kaufmann, J. Am. Chem. Soc., 114, 4937 (1992); H.-U. Siehl, F.-P. Kaufmann, and K. Hori, J. Am. Chem. Soc., 114, 9343 (1992); G. K. S. Prakash, V. P. Reddy, G. Rasul, J. Casanova, and G. A. Olah, J. Am. Chem. Soc., 114, 3076 (1992); C. S. Q. Lew and R. A. McClelland, J. Am. Chem. Soc., 115, 11516 (1993); C. Dallaire and M. A. Brook, Organometallics, 12, 2332 (1993); V. Gabelica and A. J. Kresge, J. Am. Chem. Soc., 118, 3838 (1996); W. Zhang, J. A. Stone, M. A. Brook, and G. A. McGibbon, J. Am. Chem. Soc., 118, 5764 (1996).
65. For recent examples: H.-U. Siehl, F.-P. Kaufmann, Y. Apelog, V. Braude, D. Danovish, A. Berndt, and N. Stamatis, Angew. Chem., Int. Ed. Engl., 31, 1479 (1991); H.-U. Siehl and F.-P. Kaufmann, J. Am. Chem. Soc., 114, 4937 (1992); H.-U. Siehl, F.-P. Kaufmann, and K. Hori, J. Am. Chem. Soc., 114, 9343 (1992); G. K. S. Prakash, V. P. Reddy, G. Rasul, J. Casanova, and G. A. Olah, J. Am. Chem. Soc., 114, 3076 (1992); C. S. Q. Lew and R. A. McClelland, J. Am. Chem. Soc., 115, 11516 (1993); C. Dallaire and M. A. Brook, Organometallics, 12, 2332 (1993); V. Gabelica and A. J. Kresge, J. Am. Chem. Soc., 118, 3838 (1996); W. Zhang, J. A. Stone, M. A. Brook, and G. A. McGibbon, J. Am. Chem. Soc., 118, 5764 (1996).
66. For recent examples: H.-U. Siehl, F.-P. Kaufmann, Y. Apelog, V. Braude, D. Danovish, A. Berndt, and N. Stamatis, Angew. Chem., Int. Ed. Engl., 31, 1479 (1991); H.-U. Siehl and F.-P. Kaufmann, J. Am. Chem. Soc., 114, 4937 (1992); H.-U. Siehl, F.-P. Kaufmann, and K. Hori, J. Am. Chem. Soc., 114, 9343 (1992); G. K. S. Prakash, V. P. Reddy, G. Rasul, J. Casanova, and G. A. Olah, J. Am. Chem. Soc., 114, 3076 (1992); C. S. Q. Lew and R. A. McClelland, J. Am. Chem. Soc., 115, 11516 (1993); C. Dallaire and M. A. Brook, Organometallics, 12, 2332 (1993); V. Gabelica and A. J. Kresge, J. Am. Chem. Soc., 118, 3838 (1996); W. Zhang, J. A. Stone, M. A. Brook, and G. A. McGibbon, J. Am. Chem. Soc., 118, 5764 (1996).
67. For recent examples: H.-U. Siehl, F.-P. Kaufmann, Y. Apelog, V. Braude, D. Danovish, A. Berndt, and N. Stamatis, Angew. Chem., Int. Ed. Engl., 31, 1479 (1991); H.-U. Siehl and F.-P. Kaufmann, J. Am. Chem. Soc., 114, 4937 (1992); H.-U. Siehl, F.-P. Kaufmann, and K. Hori, J. Am. Chem. Soc., 114, 9343 (1992); G. K. S. Prakash, V. P. Reddy, G. Rasul, J. Casanova, and G. A. Olah, J. Am. Chem. Soc., 114, 3076 (1992); C. S. Q. Lew and R. A. McClelland, J. Am. Chem. Soc., 115, 11516 (1993); C. Dallaire and M. A. Brook, Organometallics, 12, 2332 (1993); V. Gabelica and A. J. Kresge, J. Am. Chem. Soc., 118, 3838 (1996); W. Zhang, J. A. Stone, M. A. Brook, and G. A. McGibbon, J. Am. Chem. Soc., 118, 5764 (1996).
68. For recent examples: H.-U. Siehl, F.-P. Kaufmann, Y. Apelog, V. Braude, D. Danovish, A. Berndt, and N. Stamatis, Angew. Chem., Int. Ed. Engl., 31, 1479 (1991); H.-U. Siehl and F.-P. Kaufmann, J. Am. Chem. Soc., 114, 4937 (1992); H.-U. Siehl, F.-P. Kaufmann, and K. Hori, J. Am. Chem. Soc., 114, 9343 (1992); G. K. S. Prakash, V. P. Reddy, G. Rasul, J. Casanova, and G. A. Olah, J. Am. Chem. Soc., 114, 3076 (1992); C. S. Q. Lew and R. A. McClelland, J. Am. Chem. Soc., 115, 11516 (1993); C. Dallaire and M. A. Brook, Organometallics, 12, 2332 (1993); V. Gabelica and A. J. Kresge, J. Am. Chem. Soc., 118, 3838 (1996); W. Zhang, J. A. Stone, M. A. Brook, and G. A. McGibbon, J. Am. Chem. Soc., 118, 5764 (1996).
69. For recent examples: H.-U. Siehl, F.-P. Kaufmann, Y. Apelog, V. Braude, D. Danovish, A. Berndt, and N. Stamatis, Angew. Chem., Int. Ed. Engl., 31, 1479 (1991); H.-U. Siehl and F.-P. Kaufmann, J. Am. Chem. Soc., 114, 4937 (1992); H.-U. Siehl, F.-P. Kaufmann, and K. Hori, J. Am. Chem. Soc., 114, 9343 (1992); G. K. S. Prakash, V. P. Reddy, G. Rasul, J. Casanova, and G. A. Olah, J. Am. Chem. Soc., 114, 3076 (1992); C. S. Q. Lew and R. A. McClelland, J. Am. Chem. Soc., 115, 11516 (1993); C. Dallaire and M. A. Brook, Organometallics, 12, 2332 (1993); V. Gabelica and A. J. Kresge, J. Am. Chem. Soc., 118, 3838 (1996); W. Zhang, J. A. Stone, M. A. Brook, and G. A. McGibbon, J. Am. Chem. Soc., 118, 5764 (1996).
70. For recent examples: H.-U. Siehl, F.-P. Kaufmann, Y. Apelog, V. Braude, D. Danovish, A. Berndt, and N. Stamatis, Angew. Chem., Int. Ed. Engl., 31, 1479 (1991); H.-U. Siehl and F.-P. Kaufmann, J. Am. Chem. Soc., 114, 4937 (1992); H.-U. Siehl, F.-P. Kaufmann, and K. Hori, J. Am. Chem. Soc., 114, 9343 (1992); G. K. S. Prakash, V. P. Reddy, G. Rasul, J. Casanova, and G. A. Olah, J. Am. Chem. Soc., 114, 3076 (1992); C. S. Q. Lew and R. A. McClelland, J. Am. Chem. Soc., 115, 11516 (1993); C. Dallaire and M. A. Brook, Organometallics, 12, 2332 (1993); V. Gabelica and A. J. Kresge, J. Am. Chem. Soc., 118, 3838 (1996); W. Zhang, J. A. Stone, M. A. Brook, and G. A. McGibbon, J. Am. Chem. Soc., 118, 5764 (1996).
71. For recent examples: H.-U. Siehl, F.-P. Kaufmann, Y. Apelog, V. Braude, D. Danovish, A. Berndt, and N. Stamatis, Angew. Chem., Int. Ed. Engl., 31, 1479 (1991); H.-U. Siehl and F.-P. Kaufmann, J. Am. Chem. Soc., 114, 4937 (1992); H.-U. Siehl, F.-P. Kaufmann, and K. Hori, J. Am. Chem. Soc., 114, 9343 (1992); G. K. S. Prakash, V. P. Reddy, G. Rasul, J. Casanova, and G. A. Olah, J. Am. Chem. Soc., 114, 3076 (1992); C. S. Q. Lew and R. A. McClelland, J. Am. Chem. Soc., 115, 11516 (1993); C. Dallaire and M. A. Brook, Organometallics, 12, 2332 (1993); V. Gabelica and A. J. Kresge, J. Am. Chem. Soc., 118, 3838 (1996); W. Zhang, J. A. Stone, M. A. Brook, and G. A. McGibbon, J. Am. Chem. Soc., 118, 5764 (1996).
72. For example: G. A. Olah and S. J. Kuhn, J. Am. Chem. Soc., 80, 6541 (1958); G. A. Olah, R. H. Schlosberg, R. D. Porter, Y. K. Mo, D. P. Kelly, and G. D. Mateescu, J. Am. Chem. Soc., 94, 2034 (1972); G. A. Olah, J. S. Staral, G. Asencio, G. Liang, D. A. Forsyth, and G. D. Mateescu, J. Am. Chem. Soc., 100, 6299 (1978).
73. For example: G. A. Olah and S. J. Kuhn, J. Am. Chem. Soc., 80, 6541 (1958); G. A. Olah, R. H. Schlosberg, R. D. Porter, Y. K. Mo, D. P. Kelly, and G. D. Mateescu, J. Am. Chem. Soc., 94, 2034 (1972); G. A. Olah, J. S. Staral, G. Asencio, G. Liang, D. A. Forsyth, and G. D. Mateescu, J. Am. Chem. Soc., 100, 6299 (1978).
74. For example: G. A. Olah and S. J. Kuhn, J. Am. Chem. Soc., 80, 6541 (1958); G. A. Olah, R. H. Schlosberg, R. D. Porter, Y. K. Mo, D. P. Kelly, and G. D. Mateescu, J. Am. Chem. Soc., 94, 2034 (1972); G. A. Olah, J. S. Staral, G. Asencio, G. Liang, D. A. Forsyth, and G. D. Mateescu, J. Am. Chem. Soc., 100, 6299 (1978).
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79. R. C. Hahn and D. L. Strack, J. Am. Chem. Soc., 96, 4335 (1974); M. W. Galley and R. C. Hahn, J. Am. Chem. Soc., 96, 4337 (1974). Also see the following for the theoretical study. J. Feng, X. Zheng, and M. C. Zerner, J. Org. Chem., 51, 4531 (1986).
80. R. C. Hahn and D. L. Strack, J. Am. Chem. Soc., 96, 4335 (1974); M. W. Galley and R. C. Hahn, J. Am. Chem. Soc., 96, 4337 (1974). Also see the following for the theoretical study. J. Feng, X. Zheng, and M. C. Zerner, J. Org. Chem., 51, 4531 (1986).
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