Formation of cationic half-sandwich osmium-vinylidene complexes from [Os(η5-C5H5)(Pi Pr3)2]+ and terminal alkynes

Organometallics

Volumn 20, Issue 20, 2001, Pages 4291-4294

  Baya, Miguel ^a   Crochet, Pascale ^a   Esteruelas, Miguel A ^a   López, Ana M ^a   Modrego, Javier ^a   Oñate, Enrique ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNES; ALKYNYL DERIVATIVES; DEPROTONATION; OSMIUM-VINYLIDENE COMPLEXES; TAUTOMERIZATION;

ALKALINITY; CARRIER CONCENTRATION; ISOMERIZATION; METHANOL; OSMIUM; RUTHENIUM; STOICHIOMETRY; THERMODYNAMIC STABILITY;

ORGANOMETALLICS;

EID: 0035497138     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0104565     Document Type: Article

References (32)

1. Pourreau, D. B.; Geoffroy, G. L.; Rheingold, A. L.; Geib, S. J. Organometallics 1996, 5, 1337.
2. Esteruelas, M. A.; Gómez, A. V.; López, A. M.; Oro, L. A. Organometallics 1996, 15, 878.
3. Gamasa, M. P.; Gimeno, J.; Gónzalez-Cueva, M.; Lastra, E. J. Chem. Soc., Dalton Trans. 1996, 2547.
4. (a) Bruce, M. I. Chem. Rev. 1991, 91, 197.
5. (b) Trost, B. M. Chem. Ber. 1996, 129, 1313.
6. (c) Naota, T.; Takaya, H.; Murahashi, S.-I. Chem. Rev. 1998, 98, 2599.
7. (d) Puerta, M. C.; Valerga, P. Coord. Chem. Rev. 1999, 193-195, 977.
8. (e) Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311.
9. (f) Mitsudo, T.; Kondo, T. Synlett 2001, 309.
10. (a) Lagadec, R. L.; Roman, E.; Toupet, L.; Müller, U.; Dixneuf, P. H. Organometallics 1994, 13, 5030.
11. (b) de los Ríos, I.; Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P. J. Am. Chem. Soc. 1995, 1757.
12. (c) de los Ríos, I.; Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P. J. Am. Chem. Soc. 1997, 119, 6529.
13. (d) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Pérez-Carreño, E.; García-Granda, S. Organometallics 1999, 18, 2821.
14. (e) Bustelo, E.; Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P. Organometallics 1999, 18, 950.
15. (f) Bustelo, E.; Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P. Organometallics 1999, 18, 4563.
16. Theoretical studies support both mechanisms. (a) Silvestre, J.; Hoffmann, R. Helv. Chim. Acta 1985, 68, 1461.
17. (b) Wakatsuki, Y.; Koga, N.; Yamazaki, H.; Morokuma, K. J. Am. Chem. Soc. 1994, 116, 8105.
18. (c) Wakatsuki, Y.; Koga, N.; Werner, H.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 360.
19. (d) Stegman, R.; Frenking, G. Organometallics 1998, 17, 2089.
20. Esteruelas, M. A.; López, A. M.; Ruiz, N.; Tolosa, J. I. Organometallics 1997, 16, 4657.
21. Baya, M.; Crochet, P.; Esteruelas, M. A; Gutiérrez-Puebla, E.; López, A. M.; Modrego, J.; Oñate, E.; Vela, N. Organometallics 2000, 19, 2585.
22. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A. Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterksi, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzales, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
23. We have previously reached the same conclusion in an intuitive manner. In this context, it should be noted that the coordination of the alkyne requires a parallel approach of the caron-carbon triple bond to the phosphorous-phosphorous vector, while the oxidative addition of the alkyne should take place via a perpendicular approach of the H-C(sp) bond to the P-P vector. Furthermore, a heterolytic H-C activation of the alkyne cannot be discarded, due to the well-known acidic character of the H-C(sp) hydrogen of the alkynes.
24. Esteruelas, M. A.; Lahoz, F. J.; Oliván, M.; Oñate, E.; Oro, L. A. Organometallics 1995, 14, 3486.
25. (a) Angelici, R. J. Acc. Chem. Res. 1995, 28, 51.
26. (b) Abdur-Rashid, K.; Fong, T. P.; Greaves, B.; Gusey, D. G.; Hinman, J. G.; Landau, S. E.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2000, 122, 9155.
27. Tolman, C. A. Chem. Rev. 1977, 77, 313.
28. (a) Werner, H.; Schäfer, M.; Nürnberg, O.; Wolf, J. Chem. Ber. 1994, 127, 27.
29. (b) Esteruelas, M. A.; Lahoz, F. J.; Oñate, E.; Oro, L.A.; Rodríquez, L.; Steinert, P.; Werner, H. Organometallics 1997, 16, 6010.
30. (c) Buil, M. L.; Esteruelas, M. A.; García-Yebra, C.; Gutiérrez-Puebla, E.; Oliván, M. Organometallics 2000, 19, 2184.
31. Castarlenas, R.; Esteruelas, M. A.; Gutiérrez-Puebla, E.; Oñate, E. Organometallics 2001, 20, 1545.
32. SAINTPLUS and SHELXTL v. 6.1 software packages; Bruker Analytical X-ray Systems, Madison, WI, 2000.