An efficient synthesis of polyynyl and polyynediyl complexes of ruthenium(II)

Journal of the Chemical Society - Dalton Transactions

Volumn , Issue 21, 1999, Pages 3719-3728

  Bruce, Michael I ^a   Hall, Ben C ^a   Kelly, Brian D ^a   Low, Paul J ^a   Skelton, Brian W ^b   White, Allan H ^b  

^a UNIVERSITY OF ADELAIDE   (Australia)

^b UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748500216     PISSN: 03009246     EISSN: None     Source Type: Journal    
DOI: 10.1039/a905174k     Document Type: Article

References (92)

1. U. H. F. Bunz, Angew. Chem., Int. Ed. Engl., 1996, 35, 969;
2. H. Lang, Angew. Chem., Int. Ed. Engl., 1994, 33, 547;
3. W. Beck, B. Neimer and H. Wieser, Angew. Chem., Int. Ed. Engl., 1993, 32, 923;
4. H. Iwamura and K. Matsuda, in Modern Acetylenic Chemistry, eds. P. J. Stang and F. Diederich, VCH, Weinheim, 1995;
5. F. Paul and C. Lapinte, Coord. Chem. Rev., 1998, 178-180, 431.
6. I. R. Whittall, A. M. McDonagh, M. G. Humphrey and M. Samoc, Adv. Organomet. Chem., 1998, 42, 291;
7. S. Houbrechts, C. Boutton, K. Clays, A. Persoons, I. R. Whittall, R. H. Naulty, M. P. Cifuentes and M. G. Humphrey, J. Nonlinear Opt. Phys. Mater., 1998, 7, 113;
8. R. H. Naulty, A. M. McDonagh, I. R. Whittall, M. P. Cifuentes, M. G. Humphrey, S. Houbrechts, J. Maes, A. Persoons, G. A. Heath and D. C. R. Hockless, J. Organomet. Chem., 1998, 563, 137;
9. I. Y. Lu, J. T. Lin, J. Luo, C.-S. Li, C. Tsai, V. S. Wen, C.-C. Hsu, F.-F. Yeh and S. Liou, Organometallics, 1998, 17, 2188;
10. N. J. Long, Angew. Chem., Int. Ed. Engl., 1995, 34, 21 and refs. therein.
11. V. W.-W. Yam, J. Photochem. Photobiol. A, 1997, 106, 75;
12. V. W.-W. Yam, V. C.-Y. Lau and K.-K. Cheung, Organometallics, 1996, 15, 1740.
13. M. I. Bruce, M. Ke and P. J. Low, Chem. Commun., 1996, 2405;
14. M. I. Bruce, M. Ke, P. J. Low, B. W Skelton and A. H. White, Organometallics, 1998, 17, 3539.
15. M. I. Bruce, M. G. Humphrey, M. R. Snow and E. R. T. Tiekink, J. Organomet. Chem., 1986, 314, 213;
16. I. R. Whittall, M. G. Humphrey, A. Persoons and S. Houbrechts, Organometallics, 1996, 15, 1935.
17. W. Henderson, J. S. McIndoe, B. K. Nicholson and P. J. Dyson, J. Chem. Soc., Dalton Trans., 1998, 519.
18. K. Sonogashira, Y. Tohda and N. Hagihara, Tetrahedron Lett., 1975, 50, 4467;
19. R. F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, Orlando, 1985.
20. M. I. Bruce, P. Hinterding, E. R. T. Tiekink, B. W. Skelton and A. H. White, J. Organomet. Chem., 1993, 450, 209.
21. M. I. Bruce, B. D. Kelly, B. W Skelton and A. H. White, J. Chem. Soc., Dalton Trans., 1999, 847.
22. M. I. Bruce and P. J. Low, unpublished results.
23. M. I. Bruce, P. J. Low, B. W. Skelton and A. H. White, New J. Chem., 1998, 22, 419 and refs. therein.
24. M. I. Bruce, P. J. Low, B. W. Skelton, E. R. T. Tiekink, A. Werth and A. H. White, Aust. J. Chem., 1995, 48, 1887;
25. M. A. Bennett, M. I. Bruce and T. W. Matheson, in Comprehensive Organometallic Chemistry, eds. G. Wilkinson, F. G. A. Stone and E. W. Abel, Pergamon, Oxford, 1982, vol. 4, ch. 32.3;
26. M. A. Bennett, K. Khan and E. Wenger, in Comprehensive Organometallic Chemistry II, eds. E. W. Abel, F. G. A. Stone and G. Wilkinson, Elsevier, Oxford, 1995, vol. 7, ch. 8.
27. M. I. Bruce, Chem. Rev., 1991, 91, 197.
28. (a) M. I. Bruce, P. Hinterding, P. J. Low, B. W. Skelton and A. H. White, J. Chem. Soc., Dalton Trans., 1998, 467;
29. (b) P. Maquette, D. Touchard, L. Toupet and P. Dixneuf, J. Organomet. Chem., 1998, 565, 63.
30. (a) D. Touchard, N. Pirio, L. Toupet, M. Fettouhi, L. Ouhab and P. H. Dixneuf, Organometallics, 1995, 14, 5263;
31. (b) H. Le Bozec and P. H. Dixneuf, Russ. Chem. Bull., 1995, 44, 801;
32. (c) A. Romero, D. Peron and P. H. Dixneuf, J. Chem. Soc., Chem. Commun., 1990, 1410.
33. P. J. Kim, M. Hasai, K. Sonogashira and N. Hagihara, Inorg. Nucl. Chem. Lett., 1970, 6, 181;
34. A. Wong, P. C. W. Kang, C. D. Tagge and D. R. Leon, Organometallics, 1990, 9, 1992;
35. H. Lang and C. Weber, Organometallics, 1995, 14, 4415;
36. Y. Sun, N. J. Taylor and A. J. Carty, Organometallics, 1992, 11, 4293.
37. K. Sonogashira, T. Yatake, Y. Tohda, S. Takahashi and N. Hagihara, J. Chem. Soc., Chem. Commun., 1977, 291;
38. M. I. Bruce, M. G. Humphrey, J. G. Matisons, S. K. Roy and A. G. Swincer, Aust. J. Chem., 1984, 37, 1955.
39. K. Sonogashira, S. Kataoka, S. Takahashi and N. Hagihara, J. Organomet. Chem., 1978, 160, 319;
40. K. Sonogashira, S. Takahashi and N. Hagihara, Macromolecules, 1977, 10, 879;
41. Y. Fujikura, K. Songashira and N. Hagihara, Chem. Lett., 1975, 1067;
42. S. Takahashi, Y. Ohyama, E. Murata, K. Sonogashira and N. Hagihara, J. Polym. Sci., Polym. Chem. Ed., 1980, 18, 339.
43. R. Crescenzi and C. Lo Sterzo, Organometallics, 1992, 11, 4301.
44. O. Gervert, J. Wolf and H. Werner, Organometallics, 1996, 15, 2806.
45. J. Lewis, M. S. Khan, A. K. Kakkar, B. F. G. Johnson, T. B. Marder, H. B. Fyfe, F. Whitmann, R. H. Friend and A. E. Dray, J. Organomet. Chem., 1992, 45, 165.
46. L. Brandsma, Preparative Acetylenic Chemistry, Elsevier, Amsterdam, 1988, ch. 4.6, p. 120.
47. Z. Djeghaba, B. Jousseaume, M. Ratier and J.-G. Duboudin, J. Organomet. Chem., 1986, 304, 115.
48. J. R. Lomprey and J. P. Selegue, Organometallics, 1993, 12, 616.
49. T. Weyland, C. Lapinte, G. Frapper, M. J. Calhorda, J.-F. Halet and L. Toupet, Organometallics, 1997, 16, 2024.
50. M. I. Bruce, L. I. Denisovich, P. J. Low, S. M. Peregudova and N. A. Ustynyuk, Mendeleev Commun., 1996, 200.
51. D. Peron, A. Romero and P. H. Dixneuf, Gazz. Chim. Ital., 1994, 124, 497.
52. C. Gauss, D. Veghini and H. Berke, Chem. Ber./Recueil, 1997, 130, 183;
53. T. Rappert, O. Nürnberg and H. Werner, Organometallics, 1993, 12, 1359;
54. H. Werner, R. W. Lass, O. Gervert and J. Wolf, Organometallics, 1997, 16, 4077.
55. For some relevant papers, see: H. Werner, T. Rappert and J. Wolf, Isr. J. Chem., 1990, 30, 377;
56. B. F. G. Johnson, A. K. Kakkar, M. S. Khan and J. Lewis, J. Organomet. Chem., 1991, 409, C12;
57. H. P. Fyfe, M. Mlekuz, D. Zargarian, N. J. Taylor and T. B. Marder, J. Chem. Soc., Chem. Commun., 1991, 188;
58. P. J. Stang and R. Tykwinski, J. Am. Chem. Soc., 1992, 114, 4411;
59. N. Hagihara, K. Sonogashira and S. Takahashi, Adv. Polym. Sci., 1980, 41, 149;
60. C. C. Frazier, S. Guha, W. P. Chen, M. P. Cockerman, P. L. Porter, E. A. Chauchard and C. H. Lee, Polymer, 1987, 28, 553;
61. S. J. Davies, B. F. G. Johnson, M. S. Khan and J. Lewis, J. Chem. Soc., Chem. Commun., 1991, 187;
62. M. S. Khan, S. J. Davies, A. K. Kakkar, D. Schwartz, B. Lin, B. F. G. Johnson and J. Lewis, J. Organomet. Chem., 1992, 424, 87;
63. K. Osakada, T. Tadashi, M. Tanaka and T. Yamamoto, J. Organomet. Chem., 1994, 473, 359;
64. G. Jia, R. J. Puddephatt, T. D. Scott and J. J. Vittal, Organometallics, 1993, 12, 3656;
65. V. W.-W. Yam and S. W.-K. Choi, J. Chem. Soc., Dalton Trans., 1996, 4227.
66. O. Lavastre, M. Even, C. Troccon, P. H. Dixneuf, A. Pacreau and J.-P. Vairon, Macromol. Symp., 1997, 122, 71;
67. O. Lavastre, M. Even, P. H. Dixneuf, A. Pacreau and J.-P. Vairon, Organometallics, 1996, 15, 1530.
68. O. Lavastre, L. Olivier, P. H. Dixneuf and S. Sibandhit, Tetrahedron, 1996, 52, 5495.
69. M. Moroni, J. Le Moigne and S. Luzzati, Macromolecules, 1994, 227, 562.
70. M. I. Bruce, B. C. Hall, P. J. Low, B. W. Skelton and A. H. White, J. Organomet. Chem., in press.
71. L. Brandsma, Preparative Acetylenic Chemistry, Elsevier, Amsterdam, 1988, p. 27.
72. G. Zweifel and S. Rajagppalan, J. Am. Chem. Soc., 1985, 107, 840.
73. Y. Chi, personal communication;
74. see also: T.-K. Huang, Y. Chi, S.-M. Peng, G.-H. Lee, S.-L. Wang and F.-L. Liau, Organometallics, 1995, 14, 2164.
75. H. Werner, O. Gervert, P. Steinert and J. Wolf, Organometallics, 1995, 14, 1786.
76. J. A. Miller and G. Zweifel, Synthesis, 1983, 128.
77. T. Bartik, B. Bartik, M. Brady, R. Dembinski and J. A. Gladysz, Angew. Chem., Int. Ed. Engl., 1996, 35, 414.
78. M. Brady, W. Weng and J. A. Gladysz, J. Chem. Soc., Chem. Commun., 1994, 2655.
79. F. Coat and C. Lapinte, Organometallics, 1996, 15, 477.
80. M. Akita, M.-C. Chung, A. Sakurai, S. Sugimoto, M. Terada, M. Tanaka and Y. Moro-oka, Organometallics, 1997, 16, 4882.
81. B. F. G. Johnson, A. K. Kakkar, M. S. Khan, J. Lewis, A. E. Dray, R. H. Friend and F. Wittmann, J. Mater. Chem., 1991, 1, 485.
82. M. I. Bruce, C. Hameister, A. G. Swincer and R. C. Wallis, Inorg. Synth., 1990, 28, 270.
83. D. R. Coulson, Inorg. Synth., 1990, 28, 107.
84. G. Eglinton and W. McCrae, Adv. Org. Chem., 1963, 4, 225.
85. D. Michelot, Synth. Commun., 1983, 130.
86. J. J. Eisch and M. W. Foxton, J. Org. Chem., 1971, 36, 3520.
87. W. Hubel and R. Merenyi, Chem. Ber., 1963, 96, 930.
88. G. E. Jones, D. A. Kendrick and A. B. Holmes, Org. Synth., 1993, Coll. Vol. VIII, 63.
89. Y. Rubin, S. S. Lin, C. B. Knobler, J. Anthony, A. M. Boldi and F. Diederich, J. Am. Chem. Soc., 1991, 113, 6943.
90. A. B. Holmes and C. N. Sporikou, Org. Synth., 1993, Coll. Vol. VIII, 606.
91. B. Bartik, R. Dembinski, T. Bartik, A. M. Arif and J. A. Gladysz, New J. Chem., 1997, 21, 739.
92. S. R. Hall, G. S. D. King and J. M. Stewart, (Editors), The XTAL 3.4 Users' Manual, University of Western Australia, Lamb, Perth, 1994.