Protonation of unactivated aromatic hydrocarbons on Osmium(II): Stabilization of arenium cations via unprecedented η2- and η3-coordination

Journal of the American Chemical Society

Volumn 119, Issue 9, 1997, Pages 2096-2102

  Winemiller, Mark D ^a   Kopach, Michael E ^a   Dean Harman, W ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

METAL COMPLEX; OSMIUM;

ARTICLE; COMPLEX FORMATION; DRUG STABILITY; IN VITRO STUDY; IONIZATION; REACTION ANALYSIS;

EID: 0030993787     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963299n     Document Type: Article

References (20)

1. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry Part A: Structure and Mechanism; Plenum Press: New York, 1990.
2. Olah, G. A.; Schlosberg, R. H.; Porter, R. D.; Mo, Y. K.; D. P., K.; Mateescu, G. D. J. Am. Chem. Soc. 1972, 94, 2034.
3. Olah, G. A.; Staral, J. S.; G., A.; Liang, G.; Forsyth, D. A.; Mateescu, G. D. J. Am. Chem. Soc. 1978, 100, 6299.
4. Olah, G. A.; Mateescu, G. D.; Mo, Y. K. J. Am. Chem. Soc. 1973, 95, 1865.
5. Astruc, D. Synlett 1991, 369.
6. Semmelhack, M. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Ed.; Pergamon Press: Oxford, 1995; Vol. 12, Chapters 9.1 and 9.2.
7. Leong, V. S.; Cooper, N. J. J. Am. Chem. Soc. 1988, 110, 2644.
8. Thompson, R. L.; Lee, S.; Rheingold, A. L.; Cooper, N. J. Organometallics 1991, 10, 1657.
9. Kowalski, A. S.; Ashby, M. T. J. Am.Chem. Soc. 1995, 117, 12639.
10. Kopach, M. E.; Harman, W. D. J. Am. Chem. Soc. 1994, 116, 6581.
11. Kolis, S. P.; Gonzalez, J.; Bright, L. M.; Harman, W. D. Organometallics 1996, 15, 245.
12. Kopach, M. E.; Harman, W. D, J. Am. Chem. Soc. 1994, 59, 6506.
13. Kolis, S. P.; Kopach, M. E.; Liu, R.; Harman, W. D., submitted for publication.
14. Harman, W. D.; Hasegawa, T.; Taube, H. Inorg. Chem. 1991, 113, 453.
15. 2-2W-anisolium species, but our efforts to characterize these species were hampered by their instability.
16. Green, M. L. H.; Mitchard, L. C.; Silverthorn, W. E. J. Chem. Soc. A 1971, 2929.
17. Davison, A.; McFarlane, W.; Pratt, L.; Wilkinson, G. J. Chem. Soc. 1962, 3653.
18. 1 for the naphthalenium complex 6a varies with temperature from 1.9 (-40°C) to 2.1 (20°C).
19. Brouwer, D. M.; Mackor, E. L.; MacLean, C. In Carbonium Ions; Brouwer, D. M., Mackor, E. L., MacLean, C., Eds.; Wiley: New York, 1970; Vol. 2, pp 837.
20. Harman, W. D.; Sekine, M.; Taube, H. J. Am. Chem. Soc. 1988, 110, 5725.