Preparation and Characterization of 4-Azoniaheptatrienyl, 4-Azaheptatrienyl, Ruthenapyrrolinone, and Pyrrolinyl Complexes of Ruthenium

Organometallics

Volumn 22, Issue 25, 2003, Pages 5274-5284

  Buil, María L ^a   Esteruelas, Miguel A ^a   López, Ana M ^a   Oñate, Enrique ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

COUPLING CONSTANT; DEPROTONATION METHOD; ELECTROPHILIC CENTERS; X-RAY STRUCTURES;

ADDITION REACTIONS; AMINES; CHEMICAL BONDS; COMPLEXATION; DERIVATIVES; ETHERS; ISOMERIZATION; ISOMERS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLICS; PROTONS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); THERMAL EFFECTS; X RAY DIFFRACTION ANALYSIS;

RUTHENIUM COMPOUNDS;

EID: 0347622671     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om030518m     Document Type: Article

References (51)

1. (a) Müler, T. E.; Beller, M. Chem. Rev. 1988, 98, 675.
2. (b) Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104.
3. (c) Bytsohkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935.
4. See for example: (a) Kadota, I.; Shibuya, A.; Lutete, L. M.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4570.
5. (b) Hartung, C. G.; Tillack, A.; Trauthwein, H.; Beller, M. J. Org. Chem. 2001, 66, 6339.
6. Puerta, M. C.; Valerga, P. Coord. Chem. Rev. 1999, 193-195, 977.
7. Bruce, M. I. Chem. Rev. 1991, 91, 197.
8. (a) Gamasa, M. P.; Gimeno, J.; Martín-Vaca, B.; Borge, J.; García-Granda, S.; Pérez-Carreño, E. Organometallics 1994, 13, 4045.
9. (b) Bianchini, C.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1995, 14, 3152.
10. (c) Bianchini, C.; Purches, G.; Zanobini, F.; Peruzzini, M. Inorg. Chim. Acta 1998, 272, 2261.
11. (a) Berke, H.; Huttner, G.; Von Seyerl, J. Z. Naturforsch. 1981, 36B, 1277.
12. (b) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; González-Cueva, M.; Lastra, E.; Borge, J.; García-Granda, S.; Pérez-Carreño, E. Organometallics 1996, 15, 2137.
13. (c) Edwards, A. J.; Esteruelas, M. A.; Lahoz, F. J.; Modrego, J.; Oro, L. A.; Schrickel, J. Organometallics 1996, 15, 3556.
14. (d) Esteruelas, M. A.; Gómez, A. V.; López, A. M.; Modrego, J.; Oñate, E. Organometallics 1997, 16, 5826.
15. (e) Baya, M.; Crochet, P.; Esteruelas, M. A.; Gutiérrez-Puebla, E.; López, A. M.; Modrego, J.; Oñate, E.; Vela, N. Organometallics 2000, 19, 2585.
16. (a) Bruce, M. I. Chem. Rev. 1998, 98, 2797.
17. (b) Cadierno, V.; Gamasa, M. P.; Gimeno, J. Eur. J. Inorg. Chem. 2001, 571.
18. (c) Mantovani, N.; Marvelli, L.; Rossi, R.; Bertolasi, V.; Bianchini, C. ; de los Ríos, I.; Peruzzini, M. Organometallics 2002, 21, 2382.
19. Bernad, D. J.; Esteruelas, M. A.; López, A. M.; Modrego, J.; Puerta, M. C.; Valerga, P. Organometallics 1999, 18, 4995.
20. Esteruelas, M. A.; Gómez, A. V.; López, A. M.; Oñate; E. Organometallics 1998, 17, 3567.
21. Bernad, D. J.; Esteruelas, M. A.; López, A. M.; Oliván, M. ; Oñate, E.; Puerta, M. C.; Valerga, P. Organometallics 2000, 19, 4327.
22. Buil, M. L.; Esteruelas, M. A.; López, A. M.; Oñate, E. Organometallics 2003, 22, 162.
23. Ru enantiomer of 2 are shown.
24. (a) Bird, C. W.; Chessman, G. W. H. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 4, Part 3, p 105.
25. (b) Esteban, S.; Cornego, P.; Barthelemy, C. Química Orgánica Heterocíclica; Universidad de Educación a Distancia: Madrid, 1992; p 191.
26. (a) Esteruelas, M. A.; López, A. M. In Recent Advances in Hydride Chemistry; Peruzzini, M., Poli, R., Eds.; Elsevier: Amsterdam, 2001; Chapter 7, pp 189-284.
27. (b) Baya, M.; Buil, M. L.; Esteruelas, M. A.; López, A. M.; Oñate, E.; Rodríguez, J. R. Organometallics 2002, 21, 1841.
28. Esteruelas, M. A.; Lahoz, F. J.; Oñate, E.; Oro, L. A.; Zeir, B. Organometallics 1994, 13, 4258.
29. Jiménez-Tenorio, M. A.; Jiménez-Tenorio, M.; Puerta, M. C. ; Valerga, P. Organometallics 1997, 16, 5528.
30. Bruce, M. I.; Humphrey, M. G.; Snow, M. R.; Tiekink, E. R. T. J. Organomet. Chem. 1986, 314, 213.
31. Consiglio, G.; Morandini, F.; Ciani, G. F.; Sirani, A. Organometallics 1986, 5, 1976.
32. Bianchini, C.; Masi, D.; Romerosa, A.; Zanobini, F.; Peruzzini, M. Organometallics 1999, 18, 2376.
33. Adams, H.; Bailey, N. A.; Ridgway, C.; Taylor, B. F.; Walters, S. J.; Winter, M. J. J. Organomet. Chem. 1990, 394, 349.
34. Esteruelas, M. A.; Gómez, A. V.; Lahoz, F. J.; López, A. M.; Oñate, E.; Oro, L. A. Organometallics 1996, 15, 3423.
35. (a) Romero, A.; Santos, A.; Vegas, A. Organometattics 1988, 7, 1988.
36. (b) Löpez, J.; Santos, A.; Romero, A.; Echavarren, A. M. J. Organomet. Chem. 1993, 443, 221.
37. (c) Esteruelas, M. A.; Gómez, A. V.; López, A. M.; Modrego, J.; Oñate, E. Organometallics 1998, 17, 5434.
38. Orpen, A. G.; Brammer, L.; Allen, F. H.; Kennard, O.; Watson, D. G.; Taylor, R. J. Chem. Soc., Dalton Trans. 1989, S1.
39. (a) Sauer, J.; Prahl, H. Tetrahedron Lett. 1966, 2863.
40. (b) Riviere, M.; Lattes, A. Bull. Soc. Chim. Fr. 1968, 4430.
41. (c) Sauer, J.; Prahl, H. Chem. Ber. 1969, 102, 1917.
42. (d) Beeken, P.; Fowler, F. W. J. Org. Chem. 1980, 45, 1336.
43. (e) Eish, J. J.; Shah, J. H. J. Org. Chem. 1991, 56, 2955.
44. Fürstner, A.; Liebl, M.; Lehmann, C. W.; Picquet, M.; Kunz, R.; Bruneau, C.; Touchard, D.; Dixneuf, P. H. Chem. Eur. J. 2000, 6, 1847.
45. Andrews, P. C.; Calleja, S. M.; Maguire, M.; Nichols, P. J. Eur. J. Inorg. Chem. 2002, 1583.
46. (a) Yus, M.; Foubelo, F.; Falvello, L. R. Tetrahedron: Asymmetry 1995, 6, 2081.
47. (b) Andrews, P. C.; Calleja, S. M.; Maguire, M. J. Chem. Soc., Dalton Trans. 2002, 3640.
48. All our attempts to achieve a valid elemental analysis determination for complexes 3 and 4 were unsuccessful. Even when we tried with crystals of the same crop that was used for the X-ray diffraction study, we could not obtain a satisfactory value.
49. Blessing, R. H. Acta Cryatallogr. 1995, A51, 33-38. SADABS, Area-detector absorption correction; Bruker-AXS: Madison, WI, 1996.
50. SHELXTL Package v. 6.10; Bruker-AXS: Madison, WI, 2000. Sheldrick, G. M. SHELXS-86 and SHELXL-97; University of Göttingen: Göttingen, Germany, 1997.
51. SHELXTL Package v. 6.10; Bruker-AXS: Madison, WI, 2000. Sheldrick, G. M. SHELXS-86 and SHELXL-97; University of Göttingen: Göttingen, Germany, 1997.