Insertion of phenylacetylene into cis-silyl(stannyl)platinum complexes

Chemistry Letters

Volumn , Issue 12, 1999, Pages 1307-1308

  Ozawa, Fumiyuki ^a   Sakamoto, Yasunobu ^a   Sagawa, Takashi ^a   Tanaka, Rika ^a   Katayama, Hiroyuki ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033236844     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.1307     Document Type: Article

References (21)

1. T. N. Mitchell, H. Killing, R. Dicke, and R. Wickenkamp, J. Chem. Soc., Chem. Commun., 1985, 354; B. L. Chenard, E. D. Lagnis, F. Davidson, and T. V. RajanBabu, J. Org. Chem., 50, 3666 (1985); B. L. Chenard and C. M. Van Zyl, J. Org. Chem., 51, 3561 (1986); T. N. Mitchell, R. Wickenkamp, A. Amamria, R. Dicke, and U. Schneider, J. Org. Chem., 52, 4868 (1987): M. Murakami, Y. Morita, and Y. Ito, J. Chem. Soc., Chem. Commun., 1990, 428; Y. Tsuji and Y. Obora, J. Am. Chem. Soc., 113, 9368 (1991); Y. Obora, Y. Tsuji, M. Asayama, and T. Kawamura, Organometallics, 12, 4697 (1993); Y. Obora, Y. Tsuji, and T. Kawamura, J. Am. Chem. Soc., 117, 9814 (1995); Y. Obora, Y. Tsuji, T. Kakehi, M. Kobayashi, Y. Shinkai, M. Ebihara, and T. Kawamura, J. Chem. Soc., Perkin Trans. 1, 1995, 599.
2. T. N. Mitchell, H. Killing, R. Dicke, and R. Wickenkamp, J. Chem. Soc., Chem. Commun., 1985, 354; B. L. Chenard, E. D. Lagnis, F. Davidson, and T. V. RajanBabu, J. Org. Chem., 50, 3666 (1985); B. L. Chenard and C. M. Van Zyl, J. Org. Chem., 51, 3561 (1986); T. N. Mitchell, R. Wickenkamp, A. Amamria, R. Dicke, and U. Schneider, J. Org. Chem., 52, 4868 (1987): M. Murakami, Y. Morita, and Y. Ito, J. Chem. Soc., Chem. Commun., 1990, 428; Y. Tsuji and Y. Obora, J. Am. Chem. Soc., 113, 9368 (1991); Y. Obora, Y. Tsuji, M. Asayama, and T. Kawamura, Organometallics, 12, 4697 (1993); Y. Obora, Y. Tsuji, and T. Kawamura, J. Am. Chem. Soc., 117, 9814 (1995); Y. Obora, Y. Tsuji, T. Kakehi, M. Kobayashi, Y. Shinkai, M. Ebihara, and T. Kawamura, J. Chem. Soc., Perkin Trans. 1, 1995, 599.
3. T. N. Mitchell, H. Killing, R. Dicke, and R. Wickenkamp, J. Chem. Soc., Chem. Commun., 1985, 354; B. L. Chenard, E. D. Lagnis, F. Davidson, and T. V. RajanBabu, J. Org. Chem., 50, 3666 (1985); B. L. Chenard and C. M. Van Zyl, J. Org. Chem., 51, 3561 (1986); T. N. Mitchell, R. Wickenkamp, A. Amamria, R. Dicke, and U. Schneider, J. Org. Chem., 52, 4868 (1987): M. Murakami, Y. Morita, and Y. Ito, J. Chem. Soc., Chem. Commun., 1990, 428; Y. Tsuji and Y. Obora, J. Am. Chem. Soc., 113, 9368 (1991); Y. Obora, Y. Tsuji, M. Asayama, and T. Kawamura, Organometallics, 12, 4697 (1993); Y. Obora, Y. Tsuji, and T. Kawamura, J. Am. Chem. Soc., 117, 9814 (1995); Y. Obora, Y. Tsuji, T. Kakehi, M. Kobayashi, Y. Shinkai, M. Ebihara, and T. Kawamura, J. Chem. Soc., Perkin Trans. 1, 1995, 599.
4. T. N. Mitchell, H. Killing, R. Dicke, and R. Wickenkamp, J. Chem. Soc., Chem. Commun., 1985, 354; B. L. Chenard, E. D. Lagnis, F. Davidson, and T. V. RajanBabu, J. Org. Chem., 50, 3666 (1985); B. L. Chenard and C. M. Van Zyl, J. Org. Chem., 51, 3561 (1986); T. N. Mitchell, R. Wickenkamp, A. Amamria, R. Dicke, and U. Schneider, J. Org. Chem., 52, 4868 (1987): M. Murakami, Y. Morita, and Y. Ito, J. Chem. Soc., Chem. Commun., 1990, 428; Y. Tsuji and Y. Obora, J. Am. Chem. Soc., 113, 9368 (1991); Y. Obora, Y. Tsuji, M. Asayama, and T. Kawamura, Organometallics, 12, 4697 (1993); Y. Obora, Y. Tsuji, and T. Kawamura, J. Am. Chem. Soc., 117, 9814 (1995); Y. Obora, Y. Tsuji, T. Kakehi, M. Kobayashi, Y. Shinkai, M. Ebihara, and T. Kawamura, J. Chem. Soc., Perkin Trans. 1, 1995, 599.
5. T. N. Mitchell, H. Killing, R. Dicke, and R. Wickenkamp, J. Chem. Soc., Chem. Commun., 1985, 354; B. L. Chenard, E. D. Lagnis, F. Davidson, and T. V. RajanBabu, J. Org. Chem., 50, 3666 (1985); B. L. Chenard and C. M. Van Zyl, J. Org. Chem., 51, 3561 (1986); T. N. Mitchell, R. Wickenkamp, A. Amamria, R. Dicke, and U. Schneider, J. Org. Chem., 52, 4868 (1987): M. Murakami, Y. Morita, and Y. Ito, J. Chem. Soc., Chem. Commun., 1990, 428; Y. Tsuji and Y. Obora, J. Am. Chem. Soc., 113, 9368 (1991); Y. Obora, Y. Tsuji, M. Asayama, and T. Kawamura, Organometallics, 12, 4697 (1993); Y. Obora, Y. Tsuji, and T. Kawamura, J. Am. Chem. Soc., 117, 9814 (1995); Y. Obora, Y. Tsuji, T. Kakehi, M. Kobayashi, Y. Shinkai, M. Ebihara, and T. Kawamura, J. Chem. Soc., Perkin Trans. 1, 1995, 599.
6. T. N. Mitchell, H. Killing, R. Dicke, and R. Wickenkamp, J. Chem. Soc., Chem. Commun., 1985, 354; B. L. Chenard, E. D. Lagnis, F. Davidson, and T. V. RajanBabu, J. Org. Chem., 50, 3666 (1985); B. L. Chenard and C. M. Van Zyl, J. Org. Chem., 51, 3561 (1986); T. N. Mitchell, R. Wickenkamp, A. Amamria, R. Dicke, and U. Schneider, J. Org. Chem., 52, 4868 (1987): M. Murakami, Y. Morita, and Y. Ito, J. Chem. Soc., Chem. Commun., 1990, 428; Y. Tsuji and Y. Obora, J. Am. Chem. Soc., 113, 9368 (1991); Y. Obora, Y. Tsuji, M. Asayama, and T. Kawamura, Organometallics, 12, 4697 (1993); Y. Obora, Y. Tsuji, and T. Kawamura, J. Am. Chem. Soc., 117, 9814 (1995); Y. Obora, Y. Tsuji, T. Kakehi, M. Kobayashi, Y. Shinkai, M. Ebihara, and T. Kawamura, J. Chem. Soc., Perkin Trans. 1, 1995, 599.
7. T. N. Mitchell, H. Killing, R. Dicke, and R. Wickenkamp, J. Chem. Soc., Chem. Commun., 1985, 354; B. L. Chenard, E. D. Lagnis, F. Davidson, and T. V. RajanBabu, J. Org. Chem., 50, 3666 (1985); B. L. Chenard and C. M. Van Zyl, J. Org. Chem., 51, 3561 (1986); T. N. Mitchell, R. Wickenkamp, A. Amamria, R. Dicke, and U. Schneider, J. Org. Chem., 52, 4868 (1987): M. Murakami, Y. Morita, and Y. Ito, J. Chem. Soc., Chem. Commun., 1990, 428; Y. Tsuji and Y. Obora, J. Am. Chem. Soc., 113, 9368 (1991); Y. Obora, Y. Tsuji, M. Asayama, and T. Kawamura, Organometallics, 12, 4697 (1993); Y. Obora, Y. Tsuji, and T. Kawamura, J. Am. Chem. Soc., 117, 9814 (1995); Y. Obora, Y. Tsuji, T. Kakehi, M. Kobayashi, Y. Shinkai, M. Ebihara, and T. Kawamura, J. Chem. Soc., Perkin Trans. 1, 1995, 599.
8. T. N. Mitchell, H. Killing, R. Dicke, and R. Wickenkamp, J. Chem. Soc., Chem. Commun., 1985, 354; B. L. Chenard, E. D. Lagnis, F. Davidson, and T. V. RajanBabu, J. Org. Chem., 50, 3666 (1985); B. L. Chenard and C. M. Van Zyl, J. Org. Chem., 51, 3561 (1986); T. N. Mitchell, R. Wickenkamp, A. Amamria, R. Dicke, and U. Schneider, J. Org. Chem., 52, 4868 (1987): M. Murakami, Y. Morita, and Y. Ito, J. Chem. Soc., Chem. Commun., 1990, 428; Y. Tsuji and Y. Obora, J. Am. Chem. Soc., 113, 9368 (1991); Y. Obora, Y. Tsuji, M. Asayama, and T. Kawamura, Organometallics, 12, 4697 (1993); Y. Obora, Y. Tsuji, and T. Kawamura, J. Am. Chem. Soc., 117, 9814 (1995); Y. Obora, Y. Tsuji, T. Kakehi, M. Kobayashi, Y. Shinkai, M. Ebihara, and T. Kawamura, J. Chem. Soc., Perkin Trans. 1, 1995, 599.
9. T. N. Mitchell, H. Killing, R. Dicke, and R. Wickenkamp, J. Chem. Soc., Chem. Commun., 1985, 354; B. L. Chenard, E. D. Lagnis, F. Davidson, and T. V. RajanBabu, J. Org. Chem., 50, 3666 (1985); B. L. Chenard and C. M. Van Zyl, J. Org. Chem., 51, 3561 (1986); T. N. Mitchell, R. Wickenkamp, A. Amamria, R. Dicke, and U. Schneider, J. Org. Chem., 52, 4868 (1987): M. Murakami, Y. Morita, and Y. Ito, J. Chem. Soc., Chem. Commun., 1990, 428; Y. Tsuji and Y. Obora, J. Am. Chem. Soc., 113, 9368 (1991); Y. Obora, Y. Tsuji, M. Asayama, and T. Kawamura, Organometallics, 12, 4697 (1993); Y. Obora, Y. Tsuji, and T. Kawamura, J. Am. Chem. Soc., 117, 9814 (1995); Y. Obora, Y. Tsuji, T. Kakehi, M. Kobayashi, Y. Shinkai, M. Ebihara, and T. Kawamura, J. Chem. Soc., Perkin Trans. 1, 1995, 599.
10. M. Hada, Y. Tanaka, M. Ito, M. Murakami, H. Amii, Y. Ito, and H. Nakatsuji, J. Am. Chem. Soc., 116, 8754 (1994).
11. M. Murakami, T. Yoshida, S. Kawanami, and Y. Ito, J. Am. Chem. Soc., 117, 6408 (1995).
12. Complexes 1a-1d, 2b-2d, and 3a-3d were characterized by NMR spectroscopy and/or elemental analysis. These data are available as a supporting information (PDF) on request to the author by e-mail: ozawa@a-chem.eng.osaka-cu.ac.jp.
13. 2)) = 0.046 (0.061 ) for 4562 data with I > 3σ(I).
14. Similar distortion from planarity has heen observed for X-ray structures of his(silyl), bis(germyl), and bis(stannyl) complexes of platinum and/or palladium: Y. Tsuji, K. Nishiyama, S. Hori, M. Ebihara, and T. Kawamura, Organometallics, 17, 507 (1998); Y. Obora, Y. Tsuji, Y. Nishiyama, M. Ebihara, and T. Kawamura, J. Am. Chem. Soc., 118, 10922 (1996); H. Yamashita, T. Kobayashi, and M. Tanaka. Organometallics,. 11, 2330 (1992); W. Hatanaka, T. Wada, K. Mochida. and A. Yamamoto, 45th Symposium on Organometallic Chemistry. Japan, Tokyo, September 1998, Abstr., No. PA 137.
15. Similar distortion from planarity has heen observed for X-ray structures of his(silyl), bis(germyl), and bis(stannyl) complexes of platinum and/or palladium: Y. Tsuji, K. Nishiyama, S. Hori, M. Ebihara, and T. Kawamura, Organometallics, 17, 507 (1998); Y. Obora, Y. Tsuji, Y. Nishiyama, M. Ebihara, and T. Kawamura, J. Am. Chem. Soc., 118, 10922 (1996); H. Yamashita, T. Kobayashi, and M. Tanaka. Organometallics,. 11, 2330 (1992); W. Hatanaka, T. Wada, K. Mochida. and A. Yamamoto, 45th Symposium on Organometallic Chemistry. Japan, Tokyo, September 1998, Abstr., No. PA 137.
16. Similar distortion from planarity has heen observed for X-ray structures of his(silyl), bis(germyl), and bis(stannyl) complexes of platinum and/or palladium: Y. Tsuji, K. Nishiyama, S. Hori, M. Ebihara, and T. Kawamura, Organometallics, 17, 507 (1998); Y. Obora, Y. Tsuji, Y. Nishiyama, M. Ebihara, and T. Kawamura, J. Am. Chem. Soc., 118, 10922 (1996); H. Yamashita, T. Kobayashi, and M. Tanaka. Organometallics,. 11, 2330 (1992); W. Hatanaka, T. Wada, K. Mochida. and A. Yamamoto, 45th Symposium on Organometallic Chemistry. Japan, Tokyo, September 1998, Abstr., No. PA 137.
17. Similar distortion from planarity has heen observed for X-ray structures of his(silyl), bis(germyl), and bis(stannyl) complexes of platinum and/or palladium: Y. Tsuji, K. Nishiyama, S. Hori, M. Ebihara, and T. Kawamura, Organometallics, 17, 507 (1998); Y. Obora, Y. Tsuji, Y. Nishiyama, M. Ebihara, and T. Kawamura, J. Am. Chem. Soc., 118, 10922 (1996); H. Yamashita, T. Kobayashi, and M. Tanaka. Organometallics,. 11, 2330 (1992); W. Hatanaka, T. Wada, K. Mochida. and A. Yamamoto, 45th Symposium on Organometallic Chemistry. Japan, Tokyo, September 1998, Abstr., No. PA 137.
18. Sn-P = 1499 Hz).
19. Pt-C = 26 Hz, PtC(Ph)=CH).
20. Pt-C = 56 Hz, PtC(Ph)=CH).
21. F. Ozawa and J. Kamite, Organometallics, 17, 5630 (1998).