Silylium ions stabilized by an Si-X-Si three-center bond (X = halogen or hydrogen)

Chemistry Letters

Volumn 33, Issue 5, 2004, Pages 530-531

  Sekiguchi, Akira ^a   Murakami, Yasuyuki ^a   Fukaya, Norihisa ^a   Kabe, Yoshio ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; BORIC ACID; HALOGEN; HYDROGEN; PROPYLENE; SILICON;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLIZATION; DERIVATIZATION; MOLECULAR STABILITY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; THEORETICAL STUDY;

EID: 3242780094     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.530     Document Type: Article

References (31)

1. For the recent reviews on cations of heavier group 14 elements, see: a) J. B. Lambert, L. Kania, and S. Zhang, Chem. Rev., 95, 1191 (1995). b) C. A. Reed, Acc. Chem. Res., 31, 325 (1998). c) P. D. Lickiss, "The Chemistry of Organic Silicon Compounds," ed. by Z. Rappoport and Y. Apeloig, John Wiley & Sons Ltd., New York (1998), Vol. 2, Part I, Chap. 11. d) I. Zharov and J. Michl, "The Chemistry of Organic Germanium, Tin and Lead Compound," ed. by Z. Rappoport, John Wiley & Sons Ltd., New York (2002), Vol. 2, Part I, Chap. 10. e) J. B. Lambert, Y. Zhao, and S. M. Zhang, J. Phys. Org. Chem., 14, 370 (2001). f) A. Sekiguchi and V. Ya. Lee, Chem. Rev., 103, 1429 (2003).
2. For the recent reviews on cations of heavier group 14 elements, see: a) J. B. Lambert, L. Kania, and S. Zhang, Chem. Rev., 95, 1191 (1995). b) C. A. Reed, Acc. Chem. Res., 31, 325 (1998). c) P. D. Lickiss, "The Chemistry of Organic Silicon Compounds," ed. by Z. Rappoport and Y. Apeloig, John Wiley & Sons Ltd., New York (1998), Vol. 2, Part I, Chap. 11. d) I. Zharov and J. Michl, "The Chemistry of Organic Germanium, Tin and Lead Compound," ed. by Z. Rappoport, John Wiley & Sons Ltd., New York (2002), Vol. 2, Part I, Chap. 10. e) J. B. Lambert, Y. Zhao, and S. M. Zhang, J. Phys. Org. Chem., 14, 370 (2001). f) A. Sekiguchi and V. Ya. Lee, Chem. Rev., 103, 1429 (2003).
3. For the recent reviews on cations of heavier group 14 elements, see: a) J. B. Lambert, L. Kania, and S. Zhang, Chem. Rev., 95, 1191 (1995). b) C. A. Reed, Acc. Chem. Res., 31, 325 (1998). c) P. D. Lickiss, "The Chemistry of Organic Silicon Compounds," ed. by Z. Rappoport and Y. Apeloig, John Wiley & Sons Ltd., New York (1998), Vol. 2, Part I, Chap. 11. d) I. Zharov and J. Michl, "The Chemistry of Organic Germanium, Tin and Lead Compound," ed. by Z. Rappoport, John Wiley & Sons Ltd., New York (2002), Vol. 2, Part I, Chap. 10. e) J. B. Lambert, Y. Zhao, and S. M. Zhang, J. Phys. Org. Chem., 14, 370 (2001). f) A. Sekiguchi and V. Ya. Lee, Chem. Rev., 103, 1429 (2003).
4. For the recent reviews on cations of heavier group 14 elements, see: a) J. B. Lambert, L. Kania, and S. Zhang, Chem. Rev., 95, 1191 (1995). b) C. A. Reed, Acc. Chem. Res., 31, 325 (1998). c) P. D. Lickiss, "The Chemistry of Organic Silicon Compounds," ed. by Z. Rappoport and Y. Apeloig, John Wiley & Sons Ltd., New York (1998), Vol. 2, Part I, Chap. 11. d) I. Zharov and J. Michl, "The Chemistry of Organic Germanium, Tin and Lead Compound," ed. by Z. Rappoport, John Wiley & Sons Ltd., New York (2002), Vol. 2, Part I, Chap. 10. e) J. B. Lambert, Y. Zhao, and S. M. Zhang, J. Phys. Org. Chem., 14, 370 (2001). f) A. Sekiguchi and V. Ya. Lee, Chem. Rev., 103, 1429 (2003).
5. For the recent reviews on cations of heavier group 14 elements, see: a) J. B. Lambert, L. Kania, and S. Zhang, Chem. Rev., 95, 1191 (1995). b) C. A. Reed, Acc. Chem. Res., 31, 325 (1998). c) P. D. Lickiss, "The Chemistry of Organic Silicon Compounds," ed. by Z. Rappoport and Y. Apeloig, John Wiley & Sons Ltd., New York (1998), Vol. 2, Part I, Chap. 11. d) I. Zharov and J. Michl, "The Chemistry of Organic Germanium, Tin and Lead Compound," ed. by Z. Rappoport, John Wiley & Sons Ltd., New York (2002), Vol. 2, Part I, Chap. 10. e) J. B. Lambert, Y. Zhao, and S. M. Zhang, J. Phys. Org. Chem., 14, 370 (2001). f) A. Sekiguchi and V. Ya. Lee, Chem. Rev., 103, 1429 (2003).
6. For the recent reviews on cations of heavier group 14 elements, see: a) J. B. Lambert, L. Kania, and S. Zhang, Chem. Rev., 95, 1191 (1995). b) C. A. Reed, Acc. Chem. Res., 31, 325 (1998). c) P. D. Lickiss, "The Chemistry of Organic Silicon Compounds," ed. by Z. Rappoport and Y. Apeloig, John Wiley & Sons Ltd., New York (1998), Vol. 2, Part I, Chap. 11. d) I. Zharov and J. Michl, "The Chemistry of Organic Germanium, Tin and Lead Compound," ed. by Z. Rappoport, John Wiley & Sons Ltd., New York (2002), Vol. 2, Part I, Chap. 10. e) J. B. Lambert, Y. Zhao, and S. M. Zhang, J. Phys. Org. Chem., 14, 370 (2001). f) A. Sekiguchi and V. Ya. Lee, Chem. Rev., 103, 1429 (2003).
7. For the free silylium ions, see: a) J. B. Lambert and Y. Zhao, Angew. Chem., Int. Ed. Engl, 36, 400 (1997). b) J. B. Lambert, Y. Zhao, H. Wu, W. C. Tse, and B. Kuhlmann, J. Am. Chem. Soc., 121, 5001 (1999). c) T. Nishinaga, Y. Izukawa, and K. Komatsu, J. Am. Chem. Soc., 122, 9312 (2000). d) A. Sekiguchi, T. Matsuno, and M. Ichinohe, J. Am. Chem. Soc., 122, 11250 (2000). e) K.-C. Kim, C. A. Reed, D. W. Elliott, L. J. Mueller, F. Tham, L. Lin, and J. B. Lambert, Science, 297, 825 (2002). f) M. Nakamoto, T. Fukawa, and A. Sekiguchi, Chem. Lett., 33, 38 (2004).
8. For the free silylium ions, see: a) J. B. Lambert and Y. Zhao, Angew. Chem., Int. Ed. Engl, 36, 400 (1997). b) J. B. Lambert, Y. Zhao, H. Wu, W. C. Tse, and B. Kuhlmann, J. Am. Chem. Soc., 121, 5001 (1999). c) T. Nishinaga, Y. Izukawa, and K. Komatsu, J. Am. Chem. Soc., 122, 9312 (2000). d) A. Sekiguchi, T. Matsuno, and M. Ichinohe, J. Am. Chem. Soc., 122, 11250 (2000). e) K.-C. Kim, C. A. Reed, D. W. Elliott, L. J. Mueller, F. Tham, L. Lin, and J. B. Lambert, Science, 297, 825 (2002). f) M. Nakamoto, T. Fukawa, and A. Sekiguchi, Chem. Lett., 33, 38 (2004).
9. For the free silylium ions, see: a) J. B. Lambert and Y. Zhao, Angew. Chem., Int. Ed. Engl, 36, 400 (1997). b) J. B. Lambert, Y. Zhao, H. Wu, W. C. Tse, and B. Kuhlmann, J. Am. Chem. Soc., 121, 5001 (1999). c) T. Nishinaga, Y. Izukawa, and K. Komatsu, J. Am. Chem. Soc., 122, 9312 (2000). d) A. Sekiguchi, T. Matsuno, and M. Ichinohe, J. Am. Chem. Soc., 122, 11250 (2000). e) K.-C. Kim, C. A. Reed, D. W. Elliott, L. J. Mueller, F. Tham, L. Lin, and J. B. Lambert, Science, 297, 825 (2002). f) M. Nakamoto, T. Fukawa, and A. Sekiguchi, Chem. Lett., 33, 38 (2004).
10. For the free silylium ions, see: a) J. B. Lambert and Y. Zhao, Angew. Chem., Int. Ed. Engl, 36, 400 (1997). b) J. B. Lambert, Y. Zhao, H. Wu, W. C. Tse, and B. Kuhlmann, J. Am. Chem. Soc., 121, 5001 (1999). c) T. Nishinaga, Y. Izukawa, and K. Komatsu, J. Am. Chem. Soc., 122, 9312 (2000). d) A. Sekiguchi, T. Matsuno, and M. Ichinohe, J. Am. Chem. Soc., 122, 11250 (2000). e) K.-C. Kim, C. A. Reed, D. W. Elliott, L. J. Mueller, F. Tham, L. Lin, and J. B. Lambert, Science, 297, 825 (2002). f) M. Nakamoto, T. Fukawa, and A. Sekiguchi, Chem. Lett., 33, 38 (2004).
11. For the free silylium ions, see: a) J. B. Lambert and Y. Zhao, Angew. Chem., Int. Ed. Engl, 36, 400 (1997). b) J. B. Lambert, Y. Zhao, H. Wu, W. C. Tse, and B. Kuhlmann, J. Am. Chem. Soc., 121, 5001 (1999). c) T. Nishinaga, Y. Izukawa, and K. Komatsu, J. Am. Chem. Soc., 122, 9312 (2000). d) A. Sekiguchi, T. Matsuno, and M. Ichinohe, J. Am. Chem. Soc., 122, 11250 (2000). e) K.-C. Kim, C. A. Reed, D. W. Elliott, L. J. Mueller, F. Tham, L. Lin, and J. B. Lambert, Science, 297, 825 (2002). f) M. Nakamoto, T. Fukawa, and A. Sekiguchi, Chem. Lett., 33, 38 (2004).
12. For the free silylium ions, see: a) J. B. Lambert and Y. Zhao, Angew. Chem., Int. Ed. Engl, 36, 400 (1997). b) J. B. Lambert, Y. Zhao, H. Wu, W. C. Tse, and B. Kuhlmann, J. Am. Chem. Soc., 121, 5001 (1999). c) T. Nishinaga, Y. Izukawa, and K. Komatsu, J. Am. Chem. Soc., 122, 9312 (2000). d) A. Sekiguchi, T. Matsuno, and M. Ichinohe, J. Am. Chem. Soc., 122, 11250 (2000). e) K.-C. Kim, C. A. Reed, D. W. Elliott, L. J. Mueller, F. Tham, L. Lin, and J. B. Lambert, Science, 297, 825 (2002). f) M. Nakamoto, T. Fukawa, and A. Sekiguchi, Chem. Lett., 33, 38 (2004).
13. For the free germylium ions, see: a) A. Sekiguchi, M. Tsukamoto, and M. Ichinohe, Science, 275, 60 (1997). b) M. Ichinohe, N. Fukaya, and A. Sekiguchi, Chem. Lett., 1998, 1045. c) A. Sekiguchi, N. Fukaya, M. Ichinohe, and Y. Ishida, Eur. J. Inorg. Chem., 2000, 1155. d) A. Sekiguchi, Y. Ishida, Y. Kabe, and M. Ichinohe, J. Am. Chem. Soc., 124, 8776 (2002). e) A. Sekiguchi, T. Fukawa, V. Ya. Lee, M. Nakamoto, and M. Ichinohe, Angew. Chem., Int. Ed., 42, 1143 (2003). f) Y. Ishida, A. Sekiguchi, and Y. Kabe, J. Am. Chem. Soc., 125, 11468 (2003).
14. For the free germylium ions, see: a) A. Sekiguchi, M. Tsukamoto, and M. Ichinohe, Science, 275, 60 (1997). b) M. Ichinohe, N. Fukaya, and A. Sekiguchi, Chem. Lett., 1998, 1045. c) A. Sekiguchi, N. Fukaya, M. Ichinohe, and Y. Ishida, Eur. J. Inorg. Chem., 2000, 1155. d) A. Sekiguchi, Y. Ishida, Y. Kabe, and M. Ichinohe, J. Am. Chem. Soc., 124, 8776 (2002). e) A. Sekiguchi, T. Fukawa, V. Ya. Lee, M. Nakamoto, and M. Ichinohe, Angew. Chem., Int. Ed., 42, 1143 (2003). f) Y. Ishida, A. Sekiguchi, and Y. Kabe, J. Am. Chem. Soc., 125, 11468 (2003).
15. For the free germylium ions, see: a) A. Sekiguchi, M. Tsukamoto, and M. Ichinohe, Science, 275, 60 (1997). b) M. Ichinohe, N. Fukaya, and A. Sekiguchi, Chem. Lett., 1998, 1045. c) A. Sekiguchi, N. Fukaya, M. Ichinohe, and Y. Ishida, Eur. J. Inorg. Chem., 2000, 1155. d) A. Sekiguchi, Y. Ishida, Y. Kabe, and M. Ichinohe, J. Am. Chem. Soc., 124, 8776 (2002). e) A. Sekiguchi, T. Fukawa, V. Ya. Lee, M. Nakamoto, and M. Ichinohe, Angew. Chem., Int. Ed., 42, 1143 (2003). f) Y. Ishida, A. Sekiguchi, and Y. Kabe, J. Am. Chem. Soc., 125, 11468 (2003).
16. For the free germylium ions, see: a) A. Sekiguchi, M. Tsukamoto, and M. Ichinohe, Science, 275, 60 (1997). b) M. Ichinohe, N. Fukaya, and A. Sekiguchi, Chem. Lett., 1998, 1045. c) A. Sekiguchi, N. Fukaya, M. Ichinohe, and Y. Ishida, Eur. J. Inorg. Chem., 2000, 1155. d) A. Sekiguchi, Y. Ishida, Y. Kabe, and M. Ichinohe, J. Am. Chem. Soc., 124, 8776 (2002). e) A. Sekiguchi, T. Fukawa, V. Ya. Lee, M. Nakamoto, and M. Ichinohe, Angew. Chem., Int. Ed., 42, 1143 (2003). f) Y. Ishida, A. Sekiguchi, and Y. Kabe, J. Am. Chem. Soc., 125, 11468 (2003).
17. For the free germylium ions, see: a) A. Sekiguchi, M. Tsukamoto, and M. Ichinohe, Science, 275, 60 (1997). b) M. Ichinohe, N. Fukaya, and A. Sekiguchi, Chem. Lett., 1998, 1045. c) A. Sekiguchi, N. Fukaya, M. Ichinohe, and Y. Ishida, Eur. J. Inorg. Chem., 2000, 1155. d) A. Sekiguchi, Y. Ishida, Y. Kabe, and M. Ichinohe, J. Am. Chem. Soc., 124, 8776 (2002). e) A. Sekiguchi, T. Fukawa, V. Ya. Lee, M. Nakamoto, and M. Ichinohe, Angew. Chem., Int. Ed., 42, 1143 (2003). f) Y. Ishida, A. Sekiguchi, and Y. Kabe, J. Am. Chem. Soc., 125, 11468 (2003).
18. For the free germylium ions, see: a) A. Sekiguchi, M. Tsukamoto, and M. Ichinohe, Science, 275, 60 (1997). b) M. Ichinohe, N. Fukaya, and A. Sekiguchi, Chem. Lett., 1998, 1045. c) A. Sekiguchi, N. Fukaya, M. Ichinohe, and Y. Ishida, Eur. J. Inorg. Chem., 2000, 1155. d) A. Sekiguchi, Y. Ishida, Y. Kabe, and M. Ichinohe, J. Am. Chem. Soc., 124, 8776 (2002). e) A. Sekiguchi, T. Fukawa, V. Ya. Lee, M. Nakamoto, and M. Ichinohe, Angew. Chem., Int. Ed., 42, 1143 (2003). f) Y. Ishida, A. Sekiguchi, and Y. Kabe, J. Am. Chem. Soc., 125, 11468 (2003).
19. For the free stannylium ions, see: a) J. B. Lambert, L. Lin, S. Keinan, and T. Müller, J. Am. Chem. Soc., 125, 6022 (2003). b) A. Sekiguchi, T. Fukawa, V. Ya. Lee, and M. Nakamoto, J. Am. Chem. Soc., 125, 9250 (2003).
20. For the free stannylium ions, see: a) J. B. Lambert, L. Lin, S. Keinan, and T. Müller, J. Am. Chem. Soc., 125, 6022 (2003). b) A. Sekiguchi, T. Fukawa, V. Ya. Lee, and M. Nakamoto, J. Am. Chem. Soc., 125, 9250 (2003).
21. a) C. A. Reed, Z. Xie, R. Bau, and A. Benesi, Science, 262, 402 (1993).
22. b) Z. Xie, R. Bau, A. Benesi, and A. C. Reed, Organometallics, 14, 3933 (1995).
23. c) C. Eaborn, J. Organomet. Chem., 405, 173 (1991).
24. a) J. B. Lambert, S. Zhang, C. L. Stem, and J. C. Huffman, Science, 260, 1917 (1993).
25. b) R. Meyer, K. Werner, and T. Müller, Chem. - Eur. J., 8, 1163 (2002).
26. T. Müller, Angew. Chem., Int. Ed., 40, 3033 (2001).
27. 6, δ) -93.1, -10.8, 0.2.
28. 8, δ) 0.0, 12.7, 90.8.
29. a) G. A. Olah, G. Rasul, and G. K. S. Prakash, J. Organomet. Chem., 521, 271 (1996).
30. b) G. Frenking, S. Fau, C. M. Marchand, and H. Grüzmacher, J. Am. Chem. Soc., 119, 6648 (1997).
31. w = 0.1957 and 0.2200 for all data) for 9725 and 10939 reflections with I > 2σ(I), respectively.