Selective hydrogenation of aromatic hydrocarbons using a triruthenium carbonyl cluster as a template to control the hydrogenation site: First successful isolation of 4,5-dihydroacenaphthylene and 4,5-dihydroaceanthrylene

Journal of the American Chemical Society

Volumn 118, Issue 3, 1996, Pages 687-688

  Nagashima, Hideo ^a   Suzuki, Akihiro ^a   Nobata, Mitsuharu ^a   Itoh, Kenji ^a  

^a TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011691740     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953742e     Document Type: Article

References (20)

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2. General reviews for π-arene organometallic compounds: Silverthorn, W. E. Adv. Organomet. Chem. 1975, 13, 47. Muetterties, E. L.; Bleeke, J. R.; Wucherer, E. J.; Albright, T. A. Chem. Rev. 1982, 82, 499.
3. Reviews on π-arene organometallic compounds in organic synthesis: Watts, W. E. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, Chapter 59. Semmelhack, M. F. In New Applications of Organometallic Reagents in Organic Synthesis; Seyferth, D., Ed.; Elsevier: Amsterdam, 1976; p 361.
4. Reviews on π-arene organometallic compounds in organic synthesis: Watts, W. E. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, Chapter 59. Semmelhack, M. F. In New Applications of Organometallic Reagents in Organic Synthesis; Seyferth, D., Ed.; Elsevier: Amsterdam, 1976; p 361.
5. Recent excellent reviews on π-arene organometallic clusters: Braga, D.; Dyson, P. J.; Grepioni, F.; Johnson, B. F. G. Chem. Rev. 1994, 94, 1585. Wadepohl, H. Angew. Chem., Int. Ed. Engl. 1992, 31, 247.
6. Recent excellent reviews on π-arene organometallic clusters: Braga, D.; Dyson, P. J.; Grepioni, F.; Johnson, B. F. G. Chem. Rev. 1994, 94, 1585. Wadepohl, H. Angew. Chem., Int. Ed. Engl. 1992, 31, 247.
7. Johnson and co-workers investigated the reaction of arene osmium clusters with nucleophiles, but these did not give any more distinguished reactivities than known arene - metal compounds. Gallop, M. A.; Johnson, B. F. G.; Lewis, J.; Wright, A. H. J. Chem. Soc., Dalton Trans. 1989, 481.
8. Nagashima, H.; Fukahori, T.; Aoki, K.; Itoh, K. J. Am. Chem. Soc. 1993, 115, 10430.
9. (a) Hydrogenation of acenaphthylene: Jardine, F. H.; Osborn, J. A.; Wilkinson, G. J. Chem. Soc. A 1967, 1574. Bradley, J. S.; Hill, E.; Leonowicz, M. E.; Witzke, H. J. Mol. Catal. 1987, 41, 59. Amer, I.; Amer, H.; Ascher, R.; Blum, J.; Sasson, Y.; Vollhardt, K. P. C. J. Mol. Catal. 1987, 39, 185.
10. (a) Hydrogenation of acenaphthylene: Jardine, F. H.; Osborn, J. A.; Wilkinson, G. J. Chem. Soc. A 1967, 1574. Bradley, J. S.; Hill, E.; Leonowicz, M. E.; Witzke, H. J. Mol. Catal. 1987, 41, 59. Amer, I.; Amer, H.; Ascher, R.; Blum, J.; Sasson, Y.; Vollhardt, K. P. C. J. Mol. Catal. 1987, 39, 185.
11. (a) Hydrogenation of acenaphthylene: Jardine, F. H.; Osborn, J. A.; Wilkinson, G. J. Chem. Soc. A 1967, 1574. Bradley, J. S.; Hill, E.; Leonowicz, M. E.; Witzke, H. J. Mol. Catal. 1987, 41, 59. Amer, I.; Amer, H.; Ascher, R.; Blum, J.; Sasson, Y.; Vollhardt, K. P. C. J. Mol. Catal. 1987, 39, 185.
12. (b) Hydrogenation of aceanthrylene: Plummer, B. F.; Al-Saigh, Z. Y.; Arfan, M. J. Org. Chem. 1984, 49, 2069. Becker, H.-D.; Hansen, L.; Andersson, K. J. Org. Chem. 1985, 50, 277.
13. (b) Hydrogenation of aceanthrylene: Plummer, B. F.; Al-Saigh, Z. Y.; Arfan, M. J. Org. Chem. 1984, 49, 2069. Becker, H.-D.; Hansen, L.; Andersson, K. J. Org. Chem. 1985, 50, 277.
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16. DeWit, D. G.; Folting, K.; Streib, W. E.; Caulton, K. G. Organometallics 1985, 4, 1149. Hou, Z.; Taniguchi, H.; Fujiwara, Y. Chem. Lett. 1987, 305. Ho, K. M.; Chan, M.-C.; Luh, T.-Y. Tetrahedron Lett. 1986, 27, 5383.
17. (a) Ristagno, C. V.; Lawler, R. G. Tetrahedron Lett. 1973, 159.
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19. + 156.
20. The X-ray structures of 2b and 3b are analogous to those of 2a and 3a, respectively. See details in the supporting information.