Reactions of cis- and trans-silyl(methyl)platinum(II) complexes with phenylacetylene. Remarkable effect of cis and trans configurations on the reactivity

Organometallics

Volumn 15, Issue 21, 1996, Pages 4501-4508

  Ozawa, Fumiyuki ^a   Hikida, Toshihiko ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000597657     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960506j     Document Type: Article

References (33)

1. (a) Brunstein, P.; Knorr, M. J. Organomet. Chem. 1995, 500, 21.
2. (b) Recatto, C. A. Aldrichim. Acta 1995, 28, 85.
3. (c) Tilley, T. D. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley: Chichester, U.K., 1989; p 1415.
4. Studies on group 10 metal silyl complexes: Chatt, J.; Eaborn, C.; Kapoor, P. N. J. Organomet. Chem. 1970, 23, 109. Kiso, Y.; Tamao, K.; Kumada, M. J. Organomet. Chem. 1974, 76, 105. Eaborn, C.; Metham, T. N.; Pidcock, A. J. Organomet. Chem. 1977, 131, 377. Seyferth, D.; Goldman, E. W.; Escudié, J. J. Organomet. Chem. 1984, 271, 337. Kobayashi, T.; Hayashi, T.; Yamashita, H.; Tanaka, M. Chem. Lett. 1989, 467. Tanaka, M.; Uchimaru, Y.; Lautenschlager, H. J. Organometallics 1991, 10, 16. Pan, Y.; Mague, J. T.; Fink, M. J. Organometallics 1992, 11, 3495. Yamashita, H.; Tanaka, M.; Goto, M. Organometallics 1993, 12, 988. Murakami, M.; Yoshida, T.; Ito, Y. Organometallics 1994, 13, 2900. Suginome, M.; Oike, H.; Park, S.-S.; Ito, Y. Bull. Chem. Soc. Jpn. 1996, 69, 289.
5. Studies on group 10 metal silyl complexes: Chatt, J.; Eaborn, C.; Kapoor, P. N. J. Organomet. Chem. 1970, 23, 109. Kiso, Y.; Tamao, K.; Kumada, M. J. Organomet. Chem. 1974, 76, 105. Eaborn, C.; Metham, T. N.; Pidcock, A. J. Organomet. Chem. 1977, 131, 377. Seyferth, D.; Goldman, E. W.; Escudié, J. J. Organomet. Chem. 1984, 271, 337. Kobayashi, T.; Hayashi, T.; Yamashita, H.; Tanaka, M. Chem. Lett. 1989, 467. Tanaka, M.; Uchimaru, Y.; Lautenschlager, H. J. Organometallics 1991, 10, 16. Pan, Y.; Mague, J. T.; Fink, M. J. Organometallics 1992, 11, 3495. Yamashita, H.; Tanaka, M.; Goto, M. Organometallics 1993, 12, 988. Murakami, M.; Yoshida, T.; Ito, Y. Organometallics 1994, 13, 2900. Suginome, M.; Oike, H.; Park, S.-S.; Ito, Y. Bull. Chem. Soc. Jpn. 1996, 69, 289.
6. Studies on group 10 metal silyl complexes: Chatt, J.; Eaborn, C.; Kapoor, P. N. J. Organomet. Chem. 1970, 23, 109. Kiso, Y.; Tamao, K.; Kumada, M. J. Organomet. Chem. 1974, 76, 105. Eaborn, C.; Metham, T. N.; Pidcock, A. J. Organomet. Chem. 1977, 131, 377. Seyferth, D.; Goldman, E. W.; Escudié, J. J. Organomet. Chem. 1984, 271, 337. Kobayashi, T.; Hayashi, T.; Yamashita, H.; Tanaka, M. Chem. Lett. 1989, 467. Tanaka, M.; Uchimaru, Y.; Lautenschlager, H. J. Organometallics 1991, 10, 16. Pan, Y.; Mague, J. T.; Fink, M. J. Organometallics 1992, 11, 3495. Yamashita, H.; Tanaka, M.; Goto, M. Organometallics 1993, 12, 988. Murakami, M.; Yoshida, T.; Ito, Y. Organometallics 1994, 13, 2900. Suginome, M.; Oike, H.; Park, S.-S.; Ito, Y. Bull. Chem. Soc. Jpn. 1996, 69, 289.
7. Studies on group 10 metal silyl complexes: Chatt, J.; Eaborn, C.; Kapoor, P. N. J. Organomet. Chem. 1970, 23, 109. Kiso, Y.; Tamao, K.; Kumada, M. J. Organomet. Chem. 1974, 76, 105. Eaborn, C.; Metham, T. N.; Pidcock, A. J. Organomet. Chem. 1977, 131, 377. Seyferth, D.; Goldman, E. W.; Escudié, J. J. Organomet. Chem. 1984, 271, 337. Kobayashi, T.; Hayashi, T.; Yamashita, H.; Tanaka, M. Chem. Lett. 1989, 467. Tanaka, M.; Uchimaru, Y.; Lautenschlager, H. J. Organometallics 1991, 10, 16. Pan, Y.; Mague, J. T.; Fink, M. J. Organometallics 1992, 11, 3495. Yamashita, H.; Tanaka, M.; Goto, M. Organometallics 1993, 12, 988. Murakami, M.; Yoshida, T.; Ito, Y. Organometallics 1994, 13, 2900. Suginome, M.; Oike, H.; Park, S.-S.; Ito, Y. Bull. Chem. Soc. Jpn. 1996, 69, 289.
8. Studies on group 10 metal silyl complexes: Chatt, J.; Eaborn, C.; Kapoor, P. N. J. Organomet. Chem. 1970, 23, 109. Kiso, Y.; Tamao, K.; Kumada, M. J. Organomet. Chem. 1974, 76, 105. Eaborn, C.; Metham, T. N.; Pidcock, A. J. Organomet. Chem. 1977, 131, 377. Seyferth, D.; Goldman, E. W.; Escudié, J. J. Organomet. Chem. 1984, 271, 337. Kobayashi, T.; Hayashi, T.; Yamashita, H.; Tanaka, M. Chem. Lett. 1989, 467. Tanaka, M.; Uchimaru, Y.; Lautenschlager, H. J. Organometallics 1991, 10, 16. Pan, Y.; Mague, J. T.; Fink, M. J. Organometallics 1992, 11, 3495. Yamashita, H.; Tanaka, M.; Goto, M. Organometallics 1993, 12, 988. Murakami, M.; Yoshida, T.; Ito, Y. Organometallics 1994, 13, 2900. Suginome, M.; Oike, H.; Park, S.-S.; Ito, Y. Bull. Chem. Soc. Jpn. 1996, 69, 289.
9. Studies on group 10 metal silyl complexes: Chatt, J.; Eaborn, C.; Kapoor, P. N. J. Organomet. Chem. 1970, 23, 109. Kiso, Y.; Tamao, K.; Kumada, M. J. Organomet. Chem. 1974, 76, 105. Eaborn, C.; Metham, T. N.; Pidcock, A. J. Organomet. Chem. 1977, 131, 377. Seyferth, D.; Goldman, E. W.; Escudié, J. J. Organomet. Chem. 1984, 271, 337. Kobayashi, T.; Hayashi, T.; Yamashita, H.; Tanaka, M. Chem. Lett. 1989, 467. Tanaka, M.; Uchimaru, Y.; Lautenschlager, H. J. Organometallics 1991, 10, 16. Pan, Y.; Mague, J. T.; Fink, M. J. Organometallics 1992, 11, 3495. Yamashita, H.; Tanaka, M.; Goto, M. Organometallics 1993, 12, 988. Murakami, M.; Yoshida, T.; Ito, Y. Organometallics 1994, 13, 2900. Suginome, M.; Oike, H.; Park, S.-S.; Ito, Y. Bull. Chem. Soc. Jpn. 1996, 69, 289.
10. Studies on group 10 metal silyl complexes: Chatt, J.; Eaborn, C.; Kapoor, P. N. J. Organomet. Chem. 1970, 23, 109. Kiso, Y.; Tamao, K.; Kumada, M. J. Organomet. Chem. 1974, 76, 105. Eaborn, C.; Metham, T. N.; Pidcock, A. J. Organomet. Chem. 1977, 131, 377. Seyferth, D.; Goldman, E. W.; Escudié, J. J. Organomet. Chem. 1984, 271, 337. Kobayashi, T.; Hayashi, T.; Yamashita, H.; Tanaka, M. Chem. Lett. 1989, 467. Tanaka, M.; Uchimaru, Y.; Lautenschlager, H. J. Organometallics 1991, 10, 16. Pan, Y.; Mague, J. T.; Fink, M. J. Organometallics 1992, 11, 3495. Yamashita, H.; Tanaka, M.; Goto, M. Organometallics 1993, 12, 988. Murakami, M.; Yoshida, T.; Ito, Y. Organometallics 1994, 13, 2900. Suginome, M.; Oike, H.; Park, S.-S.; Ito, Y. Bull. Chem. Soc. Jpn. 1996, 69, 289.
11. Studies on group 10 metal silyl complexes: Chatt, J.; Eaborn, C.; Kapoor, P. N. J. Organomet. Chem. 1970, 23, 109. Kiso, Y.; Tamao, K.; Kumada, M. J. Organomet. Chem. 1974, 76, 105. Eaborn, C.; Metham, T. N.; Pidcock, A. J. Organomet. Chem. 1977, 131, 377. Seyferth, D.; Goldman, E. W.; Escudié, J. J. Organomet. Chem. 1984, 271, 337. Kobayashi, T.; Hayashi, T.; Yamashita, H.; Tanaka, M. Chem. Lett. 1989, 467. Tanaka, M.; Uchimaru, Y.; Lautenschlager, H. J. Organometallics 1991, 10, 16. Pan, Y.; Mague, J. T.; Fink, M. J. Organometallics 1992, 11, 3495. Yamashita, H.; Tanaka, M.; Goto, M. Organometallics 1993, 12, 988. Murakami, M.; Yoshida, T.; Ito, Y. Organometallics 1994, 13, 2900. Suginome, M.; Oike, H.; Park, S.-S.; Ito, Y. Bull. Chem. Soc. Jpn. 1996, 69, 289.
12. Studies on group 10 metal silyl complexes: Chatt, J.; Eaborn, C.; Kapoor, P. N. J. Organomet. Chem. 1970, 23, 109. Kiso, Y.; Tamao, K.; Kumada, M. J. Organomet. Chem. 1974, 76, 105. Eaborn, C.; Metham, T. N.; Pidcock, A. J. Organomet. Chem. 1977, 131, 377. Seyferth, D.; Goldman, E. W.; Escudié, J. J. Organomet. Chem. 1984, 271, 337. Kobayashi, T.; Hayashi, T.; Yamashita, H.; Tanaka, M. Chem. Lett. 1989, 467. Tanaka, M.; Uchimaru, Y.; Lautenschlager, H. J. Organometallics 1991, 10, 16. Pan, Y.; Mague, J. T.; Fink, M. J. Organometallics 1992, 11, 3495. Yamashita, H.; Tanaka, M.; Goto, M. Organometallics 1993, 12, 988. Murakami, M.; Yoshida, T.; Ito, Y. Organometallics 1994, 13, 2900. Suginome, M.; Oike, H.; Park, S.-S.; Ito, Y. Bull. Chem. Soc. Jpn. 1996, 69, 289.
13. Studies on group 10 metal silyl complexes: Chatt, J.; Eaborn, C.; Kapoor, P. N. J. Organomet. Chem. 1970, 23, 109. Kiso, Y.; Tamao, K.; Kumada, M. J. Organomet. Chem. 1974, 76, 105. Eaborn, C.; Metham, T. N.; Pidcock, A. J. Organomet. Chem. 1977, 131, 377. Seyferth, D.; Goldman, E. W.; Escudié, J. J. Organomet. Chem. 1984, 271, 337. Kobayashi, T.; Hayashi, T.; Yamashita, H.; Tanaka, M. Chem. Lett. 1989, 467. Tanaka, M.; Uchimaru, Y.; Lautenschlager, H. J. Organometallics 1991, 10, 16. Pan, Y.; Mague, J. T.; Fink, M. J. Organometallics 1992, 11, 3495. Yamashita, H.; Tanaka, M.; Goto, M. Organometallics 1993, 12, 988. Murakami, M.; Yoshida, T.; Ito, Y. Organometallics 1994, 13, 2900. Suginome, M.; Oike, H.; Park, S.-S.; Ito, Y. Bull. Chem. Soc. Jpn. 1996, 69, 289.
14. Recent examples other than group 10 metals: Maddock, S. M.; Rickard, C. E. F.; Roper, W. R.; Wright, L. J. Organometallics 1996, 15, 1793. Hofmann, P.; Meier, C.; Hiller, W.; Heckel, M.; Riede, J.; Schmidt, M. U. J. Organomet. Chem. 1995, 490, 51. Takao, T.; Suzuki, H.; Tanaka, M. Organometallics 1994, 13, 2554. Duckett, S.; Pertsz, R. N. Organometallics 1992, 11, 90. Wakatsuki, Y.; Yamazaki, H.; Nakano, M.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1991, 703.
15. Recent examples other than group 10 metals: Maddock, S. M.; Rickard, C. E. F.; Roper, W. R.; Wright, L. J. Organometallics 1996, 15, 1793. Hofmann, P.; Meier, C.; Hiller, W.; Heckel, M.; Riede, J.; Schmidt, M. U. J. Organomet. Chem. 1995, 490, 51. Takao, T.; Suzuki, H.; Tanaka, M. Organometallics 1994, 13, 2554. Duckett, S.; Pertsz, R. N. Organometallics 1992, 11, 90. Wakatsuki, Y.; Yamazaki, H.; Nakano, M.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1991, 703.
16. Recent examples other than group 10 metals: Maddock, S. M.; Rickard, C. E. F.; Roper, W. R.; Wright, L. J. Organometallics 1996, 15, 1793. Hofmann, P.; Meier, C.; Hiller, W.; Heckel, M.; Riede, J.; Schmidt, M. U. J. Organomet. Chem. 1995, 490, 51. Takao, T.; Suzuki, H.; Tanaka, M. Organometallics 1994, 13, 2554. Duckett, S.; Pertsz, R. N. Organometallics 1992, 11, 90. Wakatsuki, Y.; Yamazaki, H.; Nakano, M.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1991, 703.
17. Recent examples other than group 10 metals: Maddock, S. M.; Rickard, C. E. F.; Roper, W. R.; Wright, L. J. Organometallics 1996, 15, 1793. Hofmann, P.; Meier, C.; Hiller, W.; Heckel, M.; Riede, J.; Schmidt, M. U. J. Organomet. Chem. 1995, 490, 51. Takao, T.; Suzuki, H.; Tanaka, M. Organometallics 1994, 13, 2554. Duckett, S.; Pertsz, R. N. Organometallics 1992, 11, 90. Wakatsuki, Y.; Yamazaki, H.; Nakano, M.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1991, 703.
18. Recent examples other than group 10 metals: Maddock, S. M.; Rickard, C. E. F.; Roper, W. R.; Wright, L. J. Organometallics 1996, 15, 1793. Hofmann, P.; Meier, C.; Hiller, W.; Heckel, M.; Riede, J.; Schmidt, M. U. J. Organomet. Chem. 1995, 490, 51. Takao, T.; Suzuki, H.; Tanaka, M. Organometallics 1994, 13, 2554. Duckett, S.; Pertsz, R. N. Organometallics 1992, 11, 90. Wakatsuki, Y.; Yamazaki, H.; Nakano, M.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1991, 703.
19. For theoretical studies see: (a) Sakaki, S.; Ogawa, M.; Musashi, Y.; Arai, T. J. Am. Chem. Soc. 1994, 116, 7258. (b) Hada, M.; Tanaka, Y.; Ito, M.; Murakami, M.; Amii, H.; Ito, Y.; Nakatsuji, H. J. Am. Chem. Soc. 1994, 116, 8754.
20. For theoretical studies see: (a) Sakaki, S.; Ogawa, M.; Musashi, Y.; Arai, T. J. Am. Chem. Soc. 1994, 116, 7258. (b) Hada, M.; Tanaka, Y.; Ito, M.; Murakami, M.; Amii, H.; Ito, Y.; Nakatsuji, H. J. Am. Chem. Soc. 1994, 116, 8754.
21. Ozawa, F.; Sugawara, M.; Hayashi, T. Organometallics 1994, 13, 3237.
22. Sakaki, S.; Ogawa, M.; Kinoshita, M. Inorg. Chem. 1995, 99, 9933. Sakaki, S.; Ieki, M. J. Am. Chem. Soc. 1993, 115, 2373.
23. Sakaki, S.; Ogawa, M.; Kinoshita, M. Inorg. Chem. 1995, 99, 9933. Sakaki, S.; Ieki, M. J. Am. Chem. Soc. 1993, 115, 2373.
24. Ozawa, F. Hikida, T.; Hayashi, T. J. Am. Chem. Soc. 1994, 116, 2844.
25. Hikida, T.; Onitsuka, K.; Sonogashira, K.; Hayashi, T.; Ozawa, F. Chem. Lett. 1995, 985.
26. -1, ΔS‡ = 3.9 ± 1.4 eu.
27. 2Ph to the system.
28. 2Ph is trans to the methyl group. These data indirectly support the weaker Pt-R bond in 10 compared to that in 11.
29. Anderson, G. K.; Cross, R. J. Acc. Chem. Res. 1984, 17, 67. For a theoretical study, see: Sakaki, S.; Kitaura, K.; Morokuma, K.; Ohkubo, K. J. Am. Chem. Soc. 1983, 105, 2280.
30. Anderson, G. K.; Cross, R. J. Acc. Chem. Res. 1984, 17, 67. For a theoretical study, see: Sakaki, S.; Kitaura, K.; Morokuma, K.; Ohkubo, K. J. Am. Chem. Soc. 1983, 105, 2280.
31. 4a
32. Ozawa, F.; Kamite, J. Unpublished results.
33. Chatt, J.; Eaborn, C.; Ibekwe, S. D.; Kapoor, P. N. J. Chem. Soc. A 1970, 1343.