Selective synthesis of indenylruthenium(II) vinylvinylidene complexes via unstable allenylidene intermediates:Unexpected formation of alkenyl-phosphonio complexes(E)-[Ru{C(H)=C(PPh3)R}(η5-C9H7) (PPh3)2][PF6](R=1-cyclohexenyl,1-cycloheptenyl)through nucleophilic addition

Organometallics

Volumn 16, Issue 14, 1997, Pages 3178-3187

  Cadierno, Victorio ^a   Gamasa, M Pilar ^a   Gimeno, José ^a   Borge, Javier ^a   García Granda, Santiago ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000527370     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970146f     Document Type: Article

References (57)

1. (a) Bruce, M. I.; Swincer, A. G. Adv. Organomet. Chem. 1983, 22, 59.
2. (b) Bruce, M. I. Chem. Rev. 1991, 91, 197.
3. (c) Antonova, A. B.; Johansson, A. A. Russ. Chem. Rev. (Engl. Transl.) 1989, 58, 693.
4. (a) Trost, B. M. Chem. Ber. 1996, 129, 1313 and references cited therein.
5. (b) Höfer, J.; Doucet, H.; Bruneau, C; Dixneuf, P. H. Tetrohedron Lett. 1991, 32, 7409.
6. (c) Doucet, H.; Höfer, J.; Bruneau, C.; Dixneuf, P. H. J. Chem. Soc., Chem. Commun. 1993, 850.
7. (d) Rapper T.; Yamamoto, A. Organometallics 1994, 13, 4984.
8. (e) Bianchini, C.; Frediani, P.; Masi, D.; Peruzzini, M.; Zanobini, F. Organometallics 1994, 13, 4616.
9. (f) Doucet, H.; Martín-Vaca, B. M.; Bruneau, C.; Dixneuf, P. H. J. Org. Chem. 1995, 60, 7247.
10. (g) Yi, C. S.; Liu, M. Organometallics 1996, 15, 3968.
11. (h) Slugovc, C.; Mereiter, K.; Zobet, E.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 5275.
12. 2] catalyst: Trost, B. M.; Flygare, J. A. J. Am. Chem. Soc. 199 114, 5476.
13. Selegue, J. P. Organometallics 1982, 1, 217.
14. Ruthenium hydroxyvinylidene derivatives have been isolated: (a) Touchard, D.; Haquette, P.; Pirio, N.; Toupet, L.; Dixneuf, P. H. Organometallics 1993, 12, 3132. (b) Le Lagadec, R.; Roman, E.; Toupet, L.; Müller, U.; Dixneuf, P. H. Organometallics 1994, 13, 5030. (c) Braun, T.; Steinert, P.; Werner, H. J. Organomet. Chem. 1995, 488, 169. (d) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; González-Cueva, M.; Lastra, E.; Borge, J.; García-Granda, S.; Pérez-Carreño, E. Organometallics 1996, 15, 2137.
15. Ruthenium hydroxyvinylidene derivatives have been isolated: (a) Touchard, D.; Haquette, P.; Pirio, N.; Toupet, L.; Dixneuf, P. H. Organometallics 1993, 12, 3132. (b) Le Lagadec, R.; Roman, E.; Toupet, L.; Müller, U.; Dixneuf, P. H. Organometallics 1994, 13, 5030. (c) Braun, T.; Steinert, P.; Werner, H. J. Organomet. Chem. 1995, 488, 169. (d) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; González-Cueva, M.; Lastra, E.; Borge, J.; García-Granda, S.; Pérez-Carreño, E. Organometallics 1996, 15, 2137.
16. Ruthenium hydroxyvinylidene derivatives have been isolated: (a) Touchard, D.; Haquette, P.; Pirio, N.; Toupet, L.; Dixneuf, P. H. Organometallics 1993, 12, 3132. (b) Le Lagadec, R.; Roman, E.; Toupet, L.; Müller, U.; Dixneuf, P. H. Organometallics 1994, 13, 5030. (c) Braun, T.; Steinert, P.; Werner, H. J. Organomet. Chem. 1995, 488, 169. (d) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; González-Cueva, M.; Lastra, E.; Borge, J.; García-Granda, S.; Pérez-Carreño, E. Organometallics 1996, 15, 2137.
17. Ruthenium hydroxyvinylidene derivatives have been isolated: (a) Touchard, D.; Haquette, P.; Pirio, N.; Toupet, L.; Dixneuf, P. H. Organometallics 1993, 12, 3132. (b) Le Lagadec, R.; Roman, E.; Toupet, L.; Müller, U.; Dixneuf, P. H. Organometallics 1994, 13, 5030. (c) Braun, T.; Steinert, P.; Werner, H. J. Organomet. Chem. 1995, 488, 169. (d) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; González-Cueva, M.; Lastra, E.; Borge, J.; García-Granda, S.; Pérez-Carreño, E. Organometallics 1996, 15, 2137.
18. (a) Selegue, J. P.; Young, B. A.; Logan, S. L. Organometallics 1891, 10, 1972.
19. (b) Touchard, D.; Pirio, N.; Dixneuf, P. H. Organometallics 1995, 14, 4920.
20. (c) We have recently reported similar results using indenylosmium and tricarbonyltungsten derivatives: Gamasa, M. P.; Gimeno, J.; González-Cueva, M.; Lastra, E. J. Chem. Soc., Dalton Trans. 1996, 2547. Zhang, L.; Gamasa, M. P.; Gimeno, J.; Carbajo, R. J.; López-Ortiz, F.; Lanfranchi, M.; Tiripicchio, A. Organometallics 1986, 15, 4274.
21. (c) We have recently reported similar results using indenylosmium and tricarbonyltungsten derivatives: Gamasa, M. P.; Gimeno, J.; González-Cueva, M.; Lastra, E. J. Chem. Soc., Dalton Trans. 1996, 2547. Zhang, L.; Gamasa, M. P.; Gimeno, J.; Carbajo, R. J.; López-Ortiz, F.; Lanfranchi, M.; Tiripicchio, A. Organometallics 1986, 15, 4274.
22. (a) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Lastra, E. J. Organomet, Chem. 1994, 474, C27.
23. (b) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Borge, J.; García-Granda, S. J. Chem. Soc., Chem. Commun. 1994, 2495.
24. (c) Houbrechts, S.; Clays, K.; Persoons, A.; Cadierno, V.; Gamasa, M. P.; Gimeno, J. Organometallics 1996, 15, 5266.
25. Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Lastra, E.; Borge, J.; García-Granda, S. Organometallics 1994, 13, 745.
26. Gamasa, M. P.; Gimeno, J.; Martín-Vaca, B. M.; Borge, J.; García-Granda, S.; Pérez-Carreño, E. Organometallics 1994, 13, 4045.
27. Czech, P. T.; Ye, X. G.; Fenske, R. F. Organometallics 1990, 9, 2016.
28. (a) Zhou, Z.; Jablonski, C.; Bridson, J. J. Organomet. Chem. 1993, 461, 215 and references therein.
29. (b) Ceccon, A.; Elsevier, C. J.; Ernsting, J. M.; Gambaro, A.; Santi, S.; Venzo, A. Inorg. Chim. Acta 1993, 204, 15.
30. (a) Baker, R. T.; Tulip, T. H. Organometallics 1986, 5, 839.
31. (b) Kohler, F. G. Chem. Ber. 1974, 107, 570.
32. Selegue, J. P.; Lomprey, J. R. J. Am. Chem. Soc. 1992, 114, 5518.
33. Bruce, M. I.; Wong, F. S.; Shelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1982, 2203.
34. Bruce, M. I.; Humphrey, M. G.; Snow, M. R.; Tiekink, E. R. T. J. Organomet. Chem. 1986, 314, 213.
35. Borge, J.; García-Granda, S. Unpublished results.
36. (a) Schilling, B. E. R.; Hoffmann, R.; Lichtenberger, D. L. J. Am. Chem. Soc. 1979, 101, 585.
37. (b) Kostic, N. M.; Fenske, R. J. Organometallics 1982, 1, 974.
38. Ruthenium(II) cyclohexylallenylidene complexes have been trapped by addition of methanol or water to yield alkenyl-carbene derivatives: (a) Pilette, D.; Ouzzine, K.; Le Bozec, H.; Dixneuf, P. H.; Riekard, C. E. F.; Roper, W. R. Organometallics 1992, 11, 809. (b) Esteruelas, M. A.; Gómez, A. V.; Lahoz, F. J.; López, A. M.; Oñate, E.; Oro, L. A. Organometallics 1996, 15, 3423.
39. Ruthenium(II) cyclohexylallenylidene complexes have been trapped by addition of methanol or water to yield alkenyl-carbene derivatives: (a) Pilette, D.; Ouzzine, K.; Le Bozec, H.; Dixneuf, P. H.; Riekard, C. E. F.; Roper, W. R. Organometallics 1992, 11, 809. (b) Esteruelas, M. A.; Gómez, A. V.; Lahoz, F. J.; López, A. M.; Oñate, E.; Oro, L. A. Organometallics 1996, 15, 3423.
40. Bruce, M. I.; Catlow, A.; Humphrey, M. G.; Koutsantonis, G. A.; Snow, M. R.; Tiekink, E. R. T. J. Organomet. Chem. 1988, 338, 59.
41. 6] (R = 1-cyclohexenyl, 1-cycloheptenyl). Theoretical and experimental studies focused on the potential equilibrium between these complexes and the corresponding vinylidene tautomers will be undertaken.
42. Gamasa, M. P.; Gimeno, J.; González-Bernardo, C.; Borge, J.; García-Granda, S. Organometallics, in press.
43. Oro, L. A.; Ciriano, M. A.; Campo, M.; Foces-Foces, C.; Cano, F. H. J. Organomet. Chem. 1985, 289, 117.
44. Gamasa, M. P.; Gimeno, J.; González-Bernardo, C.; Martín-Vaca, B. M.; Monti, D.; Bassetti, M. Organometallics 1996, 15, 302.
45. Grant, D. F.; Gabe, E. J. J. Appl. Crystallogr. 1978, 11, 114.
46. Lehman, M. S.; Larsen, F. K. Acta Crystallogr., Sect. A 1974, 30, 580.
47. Sheldrick, G. M. SHELX86. In Crystallographic Computing 3; Sheldrick, G. M., Kruger, C., Goddard, R., Eds.; Clarendon Press: Oxford, U.K., 1985.
48. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; García-Granda, S.; Gould, R. O.; Smits, J. M. M.; Smykalla, C. The DIRDIF Program System; Technical Report; Crystallographic Laboratory, University of Nijmegen: Nijmegen, The Netherlands, 1992.
49. Sheldrick, G. M. SHELX76: Program for Crystal Structure Determination; University of Cambridge: Cambridge, U.K., 1976.
50. van der Maelen Uría, J. F. Ph.D. Thesis, University of Oviedo, 1991.
51. Walker, N.; Stuart, D. Acta Crystallogr., Sect. A 1983, 39, 158.
52. International Tables for X-Ray Crystallography; Kynoch Press: Birminghan, U.K., 1974; Vol. IV.
53. Nardelli, M. Comput. Chem. 1983, 7, 95.
54. Spek, A. L. The EUCLID Package. In Computional Crystallography; Sayre, D., Ed.; Clarendon Press: Oxford, U.K., 1982; p 528.
55. Sheldrick, G. M. SHELXL93. In Crystallographic Computing 6; Flack, P., Parkanyi, P., Simon, K., Eds.; IUCr/Oxford University Press: Oxford, U.K., 1993.
56. Parkin, S.; Moezzi, B.; Hope, H. J. Appl. Crystallogr. 1995, 28, 53.
57. van der Sluis, P.; Spek, A. L. Acta Crystallogr., Sect. A 1990, 46, 194.