Syntheses and structures of novel zerovalent ruthenium monodentate amine complexes

Journal of the Chemical Society - Dalton Transactions

Volumn , Issue 23, 1999, Pages 4231-4237

  Suzuki, Toshiaki ^a   Shiotsuki, Masashi ^a   Wada, Kenji ^a   Kondo, Teruyuki ^a   Mitsudo, Take Aki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748832376     PISSN: 03009246     EISSN: None     Source Type: Journal    
DOI: 10.1039/a907333g     Document Type: Article

References (91)

1. For examples, see: (a) M. A. Bennett, M. I. Bruce and T. W. Matheson, in Comprehensive Organometallic Chemistry, eds. G. Wilkinson, E. W. Abel and F. G. A. Stone, Pergamon, Oxford, 1982, vol. 4, ch. 32.3, pp. 691-820;
2. (b) E. A. Seddon and K. R. Seddon, in The Chemistry of Ruthenium, Elsevier, Amsterdam, 1984, ch. 8.14-8.21, pp. 221-284; ch. 9.10-9.18, pp. 366-487 and refs. therein;
3. (c) E. A. Seddon and K. R. Seddon, in The Chemistry of Ruthenium, Elsevier, Amsterdam, 1984, ch. 11.4, p. 943.
4. (a) S. Ganguly and D. M. Roundhill, Polyhedron, 1990, 9, 2517;
5. (b) Y. Qu and N. Farrell, Inorg. Chem., 1995, 34, 3573;
6. (c) K. Hiraki, T. Matsunaga and H. Kawano, Organometallics, 1994, 13, 1878.
7. C. W. Jung, J. D. Fellmann and P. E. Garrou, Organometallics, 1983, 2, 1042.
8. (a) M. Stephenson and R. J. Mawby, J. Chem. Soc., Dalton Trans., 1981, 2112;
9. (b) R. O. Gould, T. A. Stephenson and M. A. Thomson, J. Chem. Soc., Dalton Trans., 1978, 769;
10. (c) W. Heiber and P. John, Chem. Ber., 1970, 103, 2161;
11. (d) P. John, Chem. Ber., 1970, 103, 2178 and refs. therein.
12. F. Porta, C. Crotti and S. Cenini, J. Mol. Catal., 1989, 50, 333;
13. S. Cenini, F. Porta and M. Pizzotti, J. Mol. Catal., 1982, 15, 297;
14. S. Cenini, M. Pizzotti, F. Porta and G. La Monica, J. Organomet. Chem., 1977, 125, 95.
15. Y. Watanabe, Y. Tsuji, H. Ige, Y. Ohsugi and T. Ohta, J. Org. Chem., 1984, 49, 3359.
16. W. R. McWhinnie, J. D. Miller, J. B. Watts and D. Y. Waddan, Inorg. Chim. Acta, 1973, 7, 461.
17. S. Joss, H. B. Bürgi and A. Ludi, Inorg. Chem., 1985, 24, 949;
18. K. Rieder, U. Hauser, H. Siegenthaler, E. Schmidt and A. Ludi, Inorg. Chem., 1975, 14, 1902;
19. Y. Ilan and A. Kfir, Inorg. Chim. Acta, 1989, 156, 221 and refs. therein.
20. (a) H. Kurosawa, H. Asano and Y. Miyaki, Inorg. Chim. Acta, 1998, 270, 87;
21. (b) B. J. Rappoli, K. J. McGrath, C. F. George and J. C. Cooper, J. Organomet. Chem., 1993, 450, 85;
22. (c) W. Stüer, J. Wolf, H. Werner, P. Schwab and M. Schulz, Angew. Chem., Int. Ed. Engl., 1998, 37, 3421;
23. (d) J. A. Crayston, D. C. Cupertino and T. J. Dines, J. Chem. Soc., Dalton Trans., 1991, 1603;
24. (e) U. C. Sarma and P. K. Poddar, Polyhedron, 1988, 7, 1737;
25. (f) T. Rappert and A. Yamamoto, Chem. Lett., 1994, 2211.
26. A. J. Bailey and B. R. James, Chem. Commun., 1997, 505;
27. A. J. Bailey and B. R. James, Chem. Commun., 1996, 2343;
28. F. R. Keene, D. J. Salmon and T. J. Meyer, J. Am. Chem. Soc., 1976, 98, 1884.
29. T. Naota and S.-I. Murahashi, Synlett., 1991, 693;
30. Y. Watanabe, Y. Morisaki, T. Kondo and T. Mitsudo, J. Org. Chem., 1996, 61, 4214;
31. Y. Tsuji, S. Kotachi, K.-T. Huh and Y. Watanabe, J. Org. Chem., 1990, 55, 580;
32. Y. Tsuji, Y. Yokoyama, K.-T. Huh and Y. Watanabe, Bull. Chem. Soc. Jpn., 1987, 60, 3456;
33. J. A. Marsella, J. Org. Chem., 1987, 52, 467;
34. A. Arcelli, B.-T. Khai and G. Porzi, J. Organomet. Chem., 1982, 235, 93;
35. R. Grigg, T. R. B. Mitchell, S. Sutthivaiyakit and N. Tongpenyai, J. Chem. Soc., Chem. Commun., 1981, 611 and refs. therein.
36. R. Tang, S. E. Diamond, N. Neary and F. Mares, J. Chem. Soc., Chem. Commun., 1978, 562.
37. S. I. Gorelsky, E. S. Dodsworth, A. B. P. Lever and A. A. Vlcek, Coord. Chem. Rer., 1998, 174, 469;
38. V. Balzani, A. Juris, M. Venturi, S. Campagna and S. Serroni, Coord. Chem. Rev., 1996, 96, 759;
39. A. Juris, V. Balzani, F. Barigelletti, S. Campagna, P. Belser and A. von Zelewsky, Coord. Chem. Rev., 1988, 84, 85 and refs. therein.
40. (a) H. Doucet, T. Ohkuma, K. Murata, T. Yokozawa, M. Kozawa, E. Katayama, A. F. England, T. Ikariya and R. Noyori, Angew. Chem., Int. Ed, Engl., 1998, 37, 1703;
41. (b) T. Ohkuma, M. Koizumi, H. Doucet, T. Pham, M. Kozawa, K. Murata, E. Katayama, T. Yokozawa, T. Ikariya and R. Noyori, J. Am. Chem. Soc., 1998, 120, 13529;
42. (c) K. Mikami, T. Korenaga, M. Terada, T. Ohkuma, T. Pham and R. Noyori, Angew. Chem., Int. Ed., 1999, 38, 495 and refs. therein.
43. A. J. Bailey, W. P. Griffith and P. D. Savage, J. Chem. Soc., Dalton Trans., 1995, 3537;
44. W.-H. Fung, W.-C. Cheng, W.-Y. Yu, C.-M. Che and T. C. W. Mak, J. Chem. Soc., Chem. Commun., 1995, 2007;
45. A. S. Goldstein, R. H. Beer and R. S. Drago, J. Am. Chem. Soc., 1994, 116, 2424;
46. C. Augier, L. Malara, V. Lazzeri and B. Waegell, Tetrahedron Lett., 1995, 36, 8775.
47. H. Nishiyama, Y. Itoh, Y. Sugawara, H. Matsumoto, K. Aoki and K. Itoh, Bull. Chem. Soc. Jpn., 1995, 68, 1247;
48. S.-B. Park, N. Sakata and H. Nishiyama, Chem. Eur. J., 1996, 2, 303;
49. H. Nishiyama, N. Soeda, T. Naito and Y. Motoyama, Tetrahedron: Asymmetry, 1998, 9, 2865 and refs. therein.
50. H. Nishiyama, T. Shimada, H. Itoh, H. Sugiyama and Y. Motoyama, Chem. Commun., 1997, 1863;
51. W.-H. Fung, W.-Y. Yu and C.-M. Che, J. Org. Chem., 1998, 63, 7715;
52. W.-C. Cheng, W.-Y. Yu, K.-K. Cheung and C.-M. Che, J. Chem. Soc., Chem. Commun., 1994, 1063.
53. C.-J. Liu, S.-G. Li, W.-Q. Pang and C.-M. Che, Chem. Commun., 1997, 65;
54. W.-H. Leung, C.-M. Che, C.-H. Yeung and C.-K. Poon, Polyhedron, 1993, 12, 2331;
55. J. T. Groves, M. Bonchio, T. Carofiglio and K. Shalyaev, J. Am. Chem. Soc., 1996, 118, 8961;
56. J. T. Groves and R. Quinn, J. Am. Chem. Soc., 1985, 107, 5790;
57. Z. Gross, S. Ini, M. Kapon and S. Cohen, Tetrahedron Lett., 1996, 37, 7325;
58. H. Ohtake, T. Higuchi and M. Hirobe, Tetrahedron Lett., 1992, 33, 2521.
59. T. Higuchi, C. Satake and M. Hirobe, J. Am. Chem. Soc., 1995, 117, 8879;
60. E. Galardon, P. Le Maux and G. Simonneaux, Chem. Commun., 1997, 927;
61. S.-M. Au, W.-H. Fung, M.-C. Cheng, C.-M. Che and S.-M. Peng, Chem. Commun., 1997, 1665;
62. W.-C. Lo, C.-M. Che, K.-F. Cheng and T. C. W. Mak, Chem. Commun., 1997, 1205;
63. M. Frauenkron and A. Berkessel, Tetrahedron Lett., 1997, 38, 7175.
64. K. Mizushima, M. Nakaura, S.-B. Park, H. Nishiyama, H. Monjushiro, K. Harada and M. Haga, Inorg. Chim. Acta, 1997, 261, 175;
65. H. Nishiyama, S.-B. Park, M. Haga, K. Aoki and K. Itoh, Chem. Lett., 1994, 1111;
66. W.-C. Cheng, W.-Y. Yu, C.-K. Li and C.-M. Che, J. Org. Chem., 1995, 60, 6840.
67. H. Tanaka, B.-C. Tzeng, S.-M. Peng and K. Tanaka, Inorg. Chem., 1993, 32, 1508.
68. E. F. Magoon, H. C. Volger, W. W. Spooncer, J. L. von Vinkle and L. H. Slaugh, J. Organomet. Chem., 1975, 99, 135.
69. Dr. K. Tanaka, personal communication.
70. T. Suzuki, M. Shiotsuki, K. Wada, T. Kondo and Take-aki Mitsudo, Organometallics, 1999, 18, 3671.
71. T. Mitsudo, T. Suzuki, S.-W. Zhang, D. Imai, K. Fujita, T. Manabe, M. Shiotsuki, Y. Watanabe, K. Wada and T. Kondo, J. Am. Chem. Soc., 1999, 121, 1839.
72. C. K. Johnson, ORTEP II, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, TN, 1976
73. (a) M. von Wijnkoop, P. P. M. de Lange, H.-W. Frühauf, K. Vrieze, W. J. J. Smeets and A. L. Spek, Organometallics, 1995, 14, 4781;
74. (b) B. de Klerk-Engels, J. G. P. Delis, K. Vrieze, K. Goubitz and J. Fraanje, Organometallics, 1994, 13, 3269;
75. (c) B. de Klerk-Engels, J. G. P. Delis, J.-M. Ernsting, C. J. Elsevier, H.-W. Frühauf, D. J. Stufkens, K. Vrieze, K. Goubitz and J. Fraanje, Inorg. Chim. Acta, 1995, 240, 273;
76. (d) M. Helliwell, J. D. Vessey and R. J. Mawby, J. Chem. Soc., Dalton Trans., 1994, 1193;
77. (e) C. Bianchini, P. Frediani, D. Masi, M. Peruzzini and F. Zanobini, Organometallics, 1994, 13, 4616;
78. (f) F.-W. Grevels, J. G. A. Reuvers and J. Takats, J. Am. Chem. Soc., 1981, 103, 4069;
79. (g) L. Kruczynski, J. L. Martin and J. Takats, J. Organomet. Chem., 1974, 80, C9.
80. K.-M. Frosin and L. Dahlenburg, Inorg. Chim. Acta, 1990, 167, 83.
81. F. Bouachir, B. Chaudret, D. Neibecker and I. Tkatchenko, Angew. Chem., Int. Ed. Engl., 1985, 24, 347;
82. T. V. Ashworth, A. A. Chalmers, D. C. Liles, E. Meintjies and E. Singleton, Organometallics, 1987, 6, 1543;
83. J. W. Steed, D. A. Tocher and R. D. Rogers, Chem. Commun., 1996, 1589;
84. F. Bouachir, B. Chaudret and I. Tkatchenko, J. Chem. Soc., Chem. Commun., 1986, 94;
85. F. Bouachir, B. Chaudret, F. Dahan, F. Agbossou and I. Tkatchenko, Organometallics, 1991, 10, 455.
86. (a) K. Itoh, H. Nagashima, T. Ohshima, N. Oshima and H. Nishiyama, J. Organomet. Chem., 1984, 272, 179;
87. (b) P. Pertici, G. Vitulli, M. Paci and L. Porri, J. Chem. Soc., Dalton Trans., 1980, 1961.
88. (a) SIR 92, A. Altomare, M. C. Burla, M. Camalli, M. Cascarano, C. Giacovazzo, A. Guagliardi and G. Polidori, J. Appl. Crystallogr., 1994, 27, 435;
89. (b) SHELXS 86, G. M. Sheldrick, in Crystallographic Computing 3, eds. G. M. Sheldrick, C. Kruger and R. Goddard, Oxford University Press, Oxford, 1985, pp. 175-189;
90. (c) DIRDIF 94, P. T. Beurskens, G. Admiraal, G. Beurskens, W. P. Bosman, R. de Gelder, R. Israel and J. M. M. Smits, Technical Report of the Crystallography Laboratory, University of Nijmegen, 1994;
91. (d) TEXSAN, Crystal Structure Analysis Package, Molecular Structure Corp., The Woodlands, TX, 1985 and 1992.