Preparation and Characterization of an Isometallabenzene with the Structure of a 1,2,4-Cyclohexatriene

Journal of the American Chemical Society

Volumn 126, Issue 7, 2004, Pages 1946-1947

  Barrio, Pilar ^a   Esteruelas, Miguel A ^a   Oñate, Enrique ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 CYCLOHEXATRIENE; BENZENE DERIVATIVE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CHEMICAL REACTION; DRUG ISOLATION; ENANTIOMER; MOLECULAR DYNAMICS; PHASE TRANSITION; PROTEIN ANALYSIS; PROTEIN STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SPIN TRAPPING; STRUCTURE ANALYSIS;

EID: 1242264377     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja039633e     Document Type: Article

References (39)

1. Bleeke, J. R. Chem. Rev. 2001, 101, 1205.
2. (a) Elliott, G. P.; Roper, W. R.; Waters, J. M. J. Chem. Soc., Chem. Commun. 1982, 811.
3. (b) Elliott, G. P.; Mcauley, N. M.; Roper, W. R. Inorg. Synth. 1989, 26, 184.
4. (c) Rickard, C. E. F.; Roper, W. R.; Woodgate, S. D.; Wright, L. J. Angew. Chem., Int. Ed. 2000, 39, 750.
5. (a) Bleeke, J. R.; Xie, Y.-F.; Peng, W.-J.; Chiang, M. J. Am. Chem. Soc. 1989, 111, 4118.
6. (b) Bleeke, J. R. Acc. Chem. Res. 1991, 24, 271.
7. (c) Bleeke, J. R.; Xie, Y. F.; Bass, L.; Chiang, M. Y. J. Am. Chem. Soc. 1991, 113, 4703.
8. (d) Hughes, R. P.; Trujillo, H. A.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 1583.
9. (e) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Clayton, T. W., Jr.; Robinson, K. D. J. Am. Chem. Soc. 1994, 116, 4093.
10. (f) Bleeke, J. R.; Behm, R.; Xie, Y.-F.; Chiang, M. Y.; Robinson, K. D.; Beatty, A. M. Organometallics 1997, 16, 606.
11. (g) Gilbertson, R. D.; Weakley, T. J. R.; Haley, M. M. J. Am. Chem. Soc. 1999, 121, 2597.
12. (h) Hughes, R. P.; Trujillo, H. A.; Egan, J. W., Jr.; Rheingold, A. L. J. Am. Chem. Soc. 2000, 122, 2261.
13. (i) Paneque, M.; Posadas, C. M.; Poveda, M. L.; Rendón, N.; Salazar, V.; Oñate, E.; Mereiter, K. J. Am. Chem. Soc. 2003, 125, 9898.
14. Jacob, V.; Weakley, T. J. R.; Haley, M. M. Angew. Chem., Int. Ed. 2002. 41, 3470.
15. (a) Johnson, R. P. Chem. Rev. 1989, 89, 1111.
16. (b) Bettinger, H. F.; Schreiner, P. R.; Schaefer, H. F., III; Schleyer, P. v. R. J. Am. Chem. Soc. 1998, 120, 5741.
17. (c) Li, Z.; Rogers, D. W.; McLafferty, F. J.; Mandziuk, M.; Podosenin, A. V. J. Phys. Chem. A 1999, 103, 426.
18. (d) Engels, B.; Shöneboom, J. C.; Münster, A. F.; Groetsch, S. ; Christl, M. J. Am. Chem. Soc. 2002, 124, 287.
19. (a) Burrell, R. C.; Daoust, K. J.; Bradley, A. Z.; DiRico, K. J.; Johnson, R. P. J. Am. Chem. Soc. 1996, 118, 4218.
20. (b) Wills, M. S. B.; Danheiser, R. L. J. Am. Chem. Soc. 1998, 120, 9378.
21. (c) Rodríguez, D.; Navarro, A.; Castedo, L.; Domínguez, D. ; Saá, C. Org. Lett. 2000, 2, 1497.
22. (d) Rodríguez, D.; Navarro-Vázquez, A.; Castedo, L.; Domínguez, D.; Saá, C. J. Am. Chem. Soc. 2001, 123, 9178.
23. (e) Ananikov, V. P. J. Phys. Org. Chem. 2001, 14, 109.
24. (f) Ananikov, V. P. J. Phys. Org. Chem. 2003, 16, 253.
25. (a) Christl, M.; Braun, M.; Müller, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 473.
26. (b) Janoschek, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 476.
27. (c) Roth, W. R.; Hopf, H.; Horn, C. Chem. Ber. 1994, 127, 1765.
28. (d) Hopf, H.; Berger, H., Zimmermann, G.; Nüchter, U.; Jones, P. G. ; Dix, I. Angew. Chem., Int. Ed. Engl. 1997, 36, 1187.
29. Barrio, P.; Esteruelas, M. A.; Oñate, E. Organometallics 2002, 21, 2491.
30. 2, the reaction leads to a mixture of 3 and the above-mentioned derivatives.
31. 1-carbon ligands are almost invariable saturated and resist becoming unsaturated, and the presence of at least one π-donor ligand makes such unsaturated species achievable (see for example: Esteruelas, M. A.; Oro, L. A. Adv. Organomet. Chem. 2001, 47, 1). Complex 2 is a rare case of unsaturated osmium compound of this type that does not have any π-donor ligand.
32. Complex 3 is also the first cyclic metallaallene compound. For reviews of metallaallenes see: (a) Bruce, M. I. Chem. Rev. 1991, 91, 197.
33. (b) Bruce, M. I. Chem. Rev. 1998, 98, 2797.
34. (c) Puerta, M. C.; Valerga, P. Coord. Chem. Rev. 1999, 193-195, 977.
35. (d) Cadierno, V.; Gamasa, M. P.; Gimeno, J. Eur. J. Inorg. Chem. 2001, 571.
36. (a) Wen, T. B.; Zhou, Z. Y.; Jia, G. Angew. Chem., Int. Ed. 2001, 40, 1951.
37. (b) Wen, T. B.; Ng, S. M.; Hung, W. Y.; Zhou, Z. Y.; Lo, M. F.; Shek, L.-Y.; Williams, I. D.; Lin, Z.; Jia, G. J. Am. Chem. Soc. 2003, 125, 884.
38. P-C = 12.9 Hz, OsC≡).
39. Crochet, P.; Esteruelas, M. A.; López, A. M.; Martínez, M.-P.; Oliván, M.; Oñate, E.; Ruiz, N. Organometallics 1998, 17, 4500.