Novel ruthenium allenylidene and mixed alkynyl allenylidene complexes: Crystal structure of trans-[(Ph2PCH2CH2PPh2) 2Ru(C≡CPh)(=C=C=CPh2)]PF6

Organometallics

Volumn 17, Issue 18, 1998, Pages 3844-3852

  Touchard, Daniel ^a   Haquette, Pierre ^a   Daridor, Alain ^a   Romero, Antonio ^b   Dixneuf, Pierre H ^a  

^a UMR 6509 Organometalliques et Catalyse Chimie et Electrochimie Moleculaires   (France)

^b CENTRO DE INVESTIGACIONES BIOLÓGICAS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001529154     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980273r     Document Type: Article

References (118)

1. (a) Takahashi, S.; Takai, Y.; Morimoto, H.; Sonogashira, K. J. Chem. Soc., Chem. Commun. 1984, 3.
2. (b) Dembek, A. A.; Burch, R. R.; Feiring, A. E. J. Am. Chem. Soc. 1993, 115, 2087.
3. (c) Altmann, M.; Bunz, U. H. F. Angew. Chem., Int. Ed, Engl. 1995, 34, 4, 569.
4. (d) Altmann, M.; Enkelmann, V.; Lieser, G.; Bunz, U. H. F. Adv. Mater. 1995, 7, 726.
5. (e) Oriol, L.; Serrano, J. L. Adv. Mater. 1995, 7, 248.
6. (a) Dhenaut, C.; Ledoux, I.; Samuel, D. W.; Zyss, J.; Bourgault, M.; Le Bozec, H. Nature 1995, 374, 339.
7. (b) Whittall, I. R.; Humphrey, M. G.; Persoons, A.; Houbrechts, S. Organometallics 1996, 15, 5, 1935.
8. (c) Blau, W. J.; Byrne, H. J.; Cardin, D. J.; Davey, A. P. In Organic Molecules for Nonlinear Optics and Photonics; Messier, J., Kajar, F., Prasad, P., Ulrich, D., Eds.; Kluwer Academic: Dordrecht, The Netherlands, 1991, p 391.
9. (d) Blau, W. J.; Byrne, H. J.; Cardin, D. J.; Davey, A. P. J. Mater. Chem. 1991, 1, 245.
10. (e) Long, N. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 4, 21.
11. (f) Marder, S. R. In Inorganic Materials; Bruce, D. W., O'Hare, D., Eds.; Wiley: Chichester, U.K., 1992; p 115.
12. (g) Fyfe, H. B.; Mlekuz, M.; Stringer, G.; Taylor, N. J.; Marder, T. B. In Inorganic and Organometallic Polymers With Special Properties; NATO ASI Series E; Laine, R. M., Ed.; Kluwer Academic: Dordrecht, The Netherlands, 1992; Vol. 206, p 331.
13. (a) Benniston, A. C.; Goulle, V.; Harriman, A.; Lehn, J.-M.; Marczinke, B. J. Phys. Chem. 1994, 98, 7798.
14. (b) Seesler, J. L.; Wang, B.; Harrimman, A. J. Am. Chem. Soc. 1995, 117, 704.
15. (c) Harrimman, A.; Odobel, F.; Sauvage, J.-P. J. Am. Chem. Soc. 1995, 117, 9461.
16. (d) Belser, P.; Dux, R.; Baak, M.; De Cola, L.; Balzani, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 595.
17. (e) Grosshenny, V.; Harrimman, A.; Ziessel, R. Angew. Chem., Int. Ed. Engl. 1995, 34, 4, 1100.
18. (f) Crossley, M. J.; Burn, P. L.; Langford, S. J.; Prashar, K. J. Chem. Soc., Chem. Commun. 1995, 1921.
19. (g) Constable, E. C. Angew. Chem., Int. Ed. Engl. 1991, 30, 407.
20. (a) Bunz, U. H. F. Angew. Chem., Int. Ed. Engl. 1994, 33, 3, 1073.
21. (b) Bunz, U. H. F.; Enkelmann, V. Organometallics 1994, 13, 3, 3823.
22. (c) Bunz, U. H. F.; Wiegelmann-Kreiter, J. E. C. Chem. Ber. 1996, 129, 9, 785.
23. (d) Diederich, F.; Rubin, Y. Angew. Chem., Int. Ed. Engl. 1992, 31, 1101.
24. (e) Diederich, F. Nature 1994, 369, 149.
25. (f) Diederich, F. In Modern Acetylene Chemistry; Stang, P. J., Diederich, Eds.; VCH: Weinheim, Germany, 1995; p 443.
26. (g) Bunz, U. H. F. Synlett 1997, 1117.
27. (h) Faust, R.; Diederich, F.; Gramlich, V.; Seiler, P. Chem. Eur. J. 1995, 1, 111.
28. (i) Schumm, J. S.; Pearson, D. L.; Tour, J. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1360.
29. (j) Zhang, J.; Moore, J. S.; Xu, Z.; Aguirre, R. A. J. Am. Chem. Soc. 1992, 114, 2273.
30. (k) Campagna, S.; Denti, G.; Serroni, S.; Juris, A.; Venturi, M.; Riceunto, V.; Balzani, V. Chem. Eur. J. 1995, 1, 211.
31. (l) Keegstra, M. A.; De Feyter, S.; De Schryver, F. C.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1996, 35, 774.
32. (a) Weng, W.; Bartik, T.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1994, 33, 2199.
33. (b) Brady, M.; Weng, W.; Gladysz, J. A. J. Chem. Soc., Chem. Commun. 1994, 2655.
34. (c) Weyland, T.; Lapinte, C.; , Frapper, G.; Calhorda, M. J.; Halet, J.-F.; Toupet, L. Organometallics 1997, 16, 2024.
35. (d) Le Narvor, N.; Toupet, L.; Lapinte, C. J. Am. Chem. Soc. 1995, 117, 7129.
36. (e) Le Narvor, N.; Lapinte, C. Organometallics 1995, 14, 4, 634.
37. (f) Stang, P. J.; Tykwinski, R. J. Am. Chem. Soc. 1992, 114, 4411.
38. (g) Davies, S. J.; Johnson, B. F. G.; Khan, D. J.; Lewis, J. J. Chem. Soc., Chem. Commun. 1991, 187.
39. (h) Ingham, S. L.; Khan, M. S.; Lewis, J.; Long, N. J.; Raithby, P. R. J. Organomet. Chem. 1994, 470, 153.
40. (i) Faulkner, C. W.; Ingham, S. L.; Khan, M. S.; Lewis, J.; Long, N. J.; Raithby, P. R. J. Organomet. Chem. 1994, 487, 139.
41. (j) Fink, H.; Long, N. J.; Martin, A. J.; Opromolla, G.; White, A. J. P.; Williams, D. J.; Zanello, P. Organometallics 1997, 16, 2646.
42. (k) Ohshiro, N.; Takei, F.; Onitsuka, K.; Takahashi, S. Chem. Lett. 1996, 871.
43. (l) Jutzi, P.; Batz, C.; Neumann, B.; Stammler, H.-G. Angew. Chem., Int. Ed. Engl. 1996, 35, 2118.
44. (m) Astruc, D. New J. Chem. 1992, 16, 305.
45. (a) Lavastre, O.; Even, M.; Dixneuf, P. H.; Pacreau, A.; Vairon, J.-P. Organometallics 1996, 15, 1530.
46. (a) Sonogashira, K.; Kataoka, S.; Takahashi, S.; Hagihara, N. J. Organomet. Chem. 1978, 160, 319.
47. (b) Sonogashira, K.; Ohga, K.; Takahashi, S.; Hagihara, N. J. Organomet. Chem. 1980, 188, 237.
48. (c) Manners, I. Angew. Chem., Int. Ed. Engl. 1996, 35, 1603.
49. (a) Touchard, D.; Haquette, P.; Guesmi, S.; Le Pichon L.; Daridor, A.; Toupet, L.; Dixneuf, P. H. Organometallics 1997, 16, 3640.
50. (b) Lavastre, O.; Plass, J.; Bachmann, P.; Guesmi, S.; Moinet, C.; Dixneuf, P. H. Organometallics 1997, 17, 1184.
51. (a) King, R. B.; Saron, M. S. J. Chem. Soc., Chem. Commun. 1972, 1052; J. Am. Chem. Soc. 1972, 95,1817.
52. (a) King, R. B.; Saron, M. S. J. Chem. Soc., Chem. Commun. 1972, 1052; J. Am. Chem. Soc. 1972, 95,1817.
53. (b) Bruce, M. I.; Swincer, A. G. Adv. Organomet. Chem. 1983, 22, 60.
54. (c) Bruce, M. I. Chem. Rev. 1991, 91, 197.
55. (d) Kolobova, N. E.; Ivanov, L.; Zhoanho, O. S.; Derunov, V. V.; Chechulina, I. N. Izv. Akad. Nauk. SSSR, Ser. Khim. 1982, 11, 2632.
56. (a) Touchard, D.; Dixneuf, P. H. Coord. Chem. Rev. 1998, in press.
57. (b) Le Bozec, H.; Dixneuf, P. H. Russ. Chem. Rev. 1995, 44, 801.
58. (c) Dixneuf, P. H.; Bruneau, C. In Organic Synthesis via Organometallics; OSM5, Helmchen, C., Vieneg, Eds.; 1997; p 1.
59. Fischer, E. O.; Kalder, H. J.; Franck, A.; Köhler, F. H.; Huttner, G. Angew. Chem., Int. Ed. Engl. 1976, 15, 5, 623.
60. Berke, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 624.
61. Selegue, J. P. Organometallics, 1982, 1, 217.
62. (a) Pilette, D.; Ouzzine, K.; Le Bozec, H.; Dixneuf, P. H.; Richard, C. E. F.; Roper, W. R. Organometallics 1992, 11, 809.
63. (b) Ruiz, N.; Péron, D.; Sinbandith, S.; Dixneuf, P. H.; Baldoli, C.; Maiorana, S. J. Organomet. Chem. 1997, 553, 213.
64. (a) Pirio, N.; Touchard, D.; Toupet, L.; Dixneuf, P. H. J. Chem. Soc., Chem. Commun. 1991, 980.
65. (b) Pirio, N.; Touchard, D.; Dixneuf, P. H. J. Organomet. Chem. 1993, 462, C18.
66. (c) Touchard, D.; Pirio, N.; Dixneuf, P. H. Organometallics 1995, 14, 4920. See also ref 10a.
67. (a) Bruce, M. I.; Swincer, A. G. Adv. Organomet. Chem. 1983, 22, 60.
68. (b) Bruce, M. I.; Wallis, R. C. Aust. J. Chem. 1979, 32, 1471.
69. (c) Davies, S. G.; McWally, J. P.; Smallbridge, A. J. Adv. Organomet. Chem. 1990, 30, 1. See also reviews in ref 9a,c.
70. (a) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Lastra, E. J. Organomet. Chem. 1994, 474, C27.
71. (b) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Lastra, E.; Borge, J.; Garcia-Granda, S. Organometallics 1994, 13, 745.
72. (c) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Gonzalez-Cueva, M.; Lastra, E.; Borge, J.; Garcia-Granda, S.; Perez-Carreno, E. Organometallics 1996, 15, 2137.
73. (d) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Lopez-Gonzales, M. C.; Borge, J.; Garcia-Granda, S. Organometallics 1997, 16, 4453.
74. (e) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Borge, J.; Garcia-Granda, S. Organometallics 1997, 16, 3178.
75. (f) Gamasa, M. P.; Gimeno, J.; Gonzales-Bernardo, C.; Borge, J.; Garcia-Granda, S. Organometallics 1997, 16, 2483.
76. (g) Touchard, D.; Pirio, N.; Toupet, L.; Fettouhi, M.; Ouahab, L.; Dixneuf, P. H. Organometallics 1995, 14, 5263.
77. (h) Lomprey, J. R.; Selegue, J. P. Organometallics 1993, 12, 616.
78. (a) Werner, H.; Stark, A.; Steinert, P.; Grünwald, C.; Wolf, J. Chem. Ber. 1995, 128, 49.
79. (b) Braun, T.; Steinert, P.; Werner, H. J. Organomet. Chem. 1995, 488, 169.
80. Nakanishi, S.; Goda, K. I.; Uchiyoma, S. I.; Otsuji, Y. Bull. Chem. Soc. Jpn. 1992, 65, 2560.
81. (a) Berke, H. Chem. Ber. 1980, 113, 1370.
82. (b) Berke, H.; Härter, P.; Hutter, G.; Seyerl, J. V. J. Organomet. Chem. 1981, 219, 317.
83. (c) Fischer, H.; Roth, G.; Reindl, D.; Troll, C. J. Organomet. Chem. 1993, 454, 133.
84. (d) Fischer, H.; Reindl, D.; Roth, G. Z. Naturforsch. 1994, 49b, 1207.
85. (e) Roth, G.; Fischer, H. J. Organomet. Chem. 1996, 507, 125.
86. (f) Roth, G.; Fischer, H. Organometallics 1996, 15, 1139.
87. Duetsch, M.; Stein, F.; Lackman, R.; Pohl, E.; Herbst-Irmer, R.; de Meijere, A. Chem. Ber. 1992, 125, 2051.
88. Tamm, M. Organometallics 1997, 16, 1418 and references therein.
89. (a) Windmüller, B.; Wolf, J.; Werner, H. J. Organomet. Chem. 1995, 502, 147.
90. (b) Werner, H.; Laubender, M.; Wiedemann, R.; Windmuller, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1237.
91. (c) Wiedemann, R.; Steinert, P.; Gevert, O.; Werner, H. J. Am. Chem. Soc. 1996, 118, 2495.
92. (d) Werner, H.; Wiedemann, R.; Mahr, N.; Steinert, P.; Wolf, J. Chem. Eur. J. 1996, 2, 561.
93. (e) Werner, H.; Wiedemann, R.; Laubender, M.; Wolf, J.; Windmuller, B. J. Chem. Soc., Chem. Commun. 1996, 1413 and cited references.
94. (a) Esteruelas, M. A.; Oro, L. A.; Schrikel, J. Organometallics 1997, 16, 796.
95. (b) Esteruelas, M. A.; Gomez, A. V.; Lopez, A. M.; Modrego, J.; Onate, E. Organometallics 1997, 16, 5826.
96. (c) Bohanna, C.; Callejas, B.; Edwards, A. J.; Esteruelas, M. A.; Lahoz, F. J.; Oro, L. A.; Ruiz, N.; Valero, C. Organometallics 1998, 17, 373.
97. (a) Touchard, D.; Guesmi, S.; Bouchaib, M.; Maquette, P.; Daridor, A.; Dixneuf, P. H. Organometallics 1996, 15, 2579.
98. (b) Capon, J. F.; Le Berre-Cosquer, N.; Leblanc, B.; Kergoat, R. J. Organomet. Chem. 1996, 508, 31.
99. (a) Xia, H. P.; Jia, G. Organometallics 1997, 1, 16.
100. (b) Jia, G.; Xia, H. P.; Wu, W. F.; Sang Ng, W. Organometallics 1996, 15, 3634.
101. (c) Xia, H. P.; Wu, W. F.; Sang Ng, W.; Williams, I. D.; Jia, G. Organometallics 1997, 16, 2940.
102. (a) Guesmi, S.; Touchard, D.; Dixneuf, P. H. J. Chem. Soc., Chem. Commun. 1996, 2773.
103. (b) Lebreton C.; Touchard, D.; Le Pichon, L.; Daridor, A.; Toupet, L.; Dixneuf, P. H. Inorg. Chim. Acta, 1998, in press.
104. (a) Albertin, G.; Antonuitti, S.; Bordignon, E.; Cazzaro, F.; Ianelli, S.; Pellizi, G. Organometallics 1995, 14, 4114.
105. (b) Werner, H.; Wiedemann, R.; Mahr, N.; Steinert, P.; Wolf, J. Chem. Eur. J. 1996, 2, 561.
106. Touchard, D.; Morice, C.; Cadierno, V.; Haquette, P.; Toupet, L.; Dixneuf, P. H. J. Chem. Soc., Chem. Commun. 1994, 859.
107. Werner, H. J. Chem. Soc., Chem. Commun. 1997, 903 and cited references.
108. Chin, B.; Lough, A. J.; Morris, R. H.; Sheitzer, C. T.; D'Agostino, C. Inorg. Chem. 1994, 33, 6278.
109. Touchard, D.; Guesmi, S.; Le Pichon, L.; Daridor, A.; Dixneuf, P. H. Inorg. Chim. Acta, 1998, in press.
110. Wolinska, A.; Touchard, D.; Dixneuf, P. H.; Romero, A. J. Organomet. Chem. 1991, 420, 217.
111. Touchard, D.; Haquette, P.; Pirio, N.; Toupet, L.; Dixneuf, P. H. Organometallics 1993, 12, 3132.
112. Bruce, M. I.; Humphrey, H. G.; Snow, H. R.; Tiekink, E. R. T. J. Organomet. Chem. 1986, 314, 213.
113. Chaudret, B.; Commenges, G.; Poilblanc, R. J. Chem. Soc., Dalton Trans. 1984, 1635.
114. Brandsma, L. Preparative Acetylenic Chemistry; Elsevier: Amsterdam, 1988.
115. Walker, N.; Stuart, D. Acta Crystallogr., Sect. A 1987, 39, 158.
116. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, England, 1974; Vol. IV.
117. Stewart, J. M., Ed. The X-ray System of Crystallographic Programs; University of Maryland: College Park, MD, 1978.
118. Berskens, P.; Bosman, W. P.; Doesburg, H. H.; Gould, R. O.; Van den Hark, T. E. M.; Prick, P. A. J.; Noordik, J. H.; Parthasarati, V.; Bruins Slot, H. J.; Haltiwanger, R. C.; Smits, J. M. M. Dirdif System; Crystallography Toernooivel: Nijmegen, The Netherlands, 1984.