A Double Carbon-Carbon Bond Activation of 8-Quinolinyl Cyclopropyl Ketone by Chlorobis(ethylene)rhodium(I) Dimer

Bulletin of the Korean Chemical Society

Volumn 24, Issue 8, 2003, Pages 1059-1060

  Lee, Dae Yon ^a   Jun, Chul Ho ^a  

^a Yonsei University   (South Korea)

Author keywords

C C bond activation; Cyclopropyl; Ketone; Quinoline; Rhodium

Indexed keywords

8 QUINOLINYLCYCLOPROPYL KETONE; 8 QUINOLINYLPENTENYL KETONE; 8 QUINOLINYLPROPENYL KETONE; BENZENE; CARBONYL DERIVATIVE; CHLOROBIS(ETHYLENE)RHODIUM; CYCLOPROPANE DERIVATIVE; DIMER; ETHYLENE DERIVATIVE; ORGANOMETALLIC COMPOUND; QUINOLINE DERIVATIVE; RHODIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHELATION; CHEMICAL BOND; CHEMICAL STRUCTURE; ELIMINATION REACTION; ISOMERISM; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION; SYNTHESIS; TEMPERATURE;

EID: 0345307097     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2003.24.8.1059     Document Type: Article

References (31)

1. For reviews, see: (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245.
2. (b) Rybtchinski, B.; Milstein, D. Angew. Chem. Int. Ed. 1999, 38, 870.
3. (c) Jennings, P. W.; Johnson, L. L. Chem. Rev. 1999, 94, 2241.
4. (d) Murakami, M.; Ito, Y. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: Berlin, German, 1999; pp 97-129.
5. (a) Bishop, K. C. Chem. Rev. 1976, 76, 461.
6. (b) Periana, P. A.; Bergman, R. G. J. Am. Chem. Soc. 1984, 106, 7272.
7. (c) Murakami, M.; Ami, H.; Ito, Y. Nature 1994, 370, 540.
8. (d) Edelbach, B. L.; Lachicotte, R. J.; Jones, W. D. J. Am. Chem. Soc. 1998, 120, 2843.
9. (e) Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 1999, 121, 11010.
10. (f) Murakami, M.; Tsuruta, T.; Ito, Y. Angew. Chem. Int. Ed. 2000, 39, 2484.
11. (a) Bruce, M. I. Angew. Chem., Int. Ed. Engl. 1977, 16, 73.
12. (b) Ryabov, A. D. Chem. Rev. 1990, 90, 403.
13. (c) Jun, C.-H.; Hong, J.-B.; Lee, D.-Y. Synlett 1999, 1.
14. (d) Jun, C.-H.; Moon, C. W.; Lee, D.-Y. Chem. Eur. J. 2002, 8, 2423.
15. (a) Jun, C.-H. J. Organomet. Chem. 1990, 390, 361.
16. (b) Jun, C.-H.; Kang, J.-B.; Lim, Y.-G., Tetrahedron Lett. 1995, 36, 277.
17. (c) Jun, C.-H. Organometallics 1996, 15, 895.
18. (d) Lee, D.-Y.; Lim, Y.-G.; Jun, C.-H. Bull. Korean Chem. Soc. 1997, 18, 824.
19. (a) Joule, J. A.; Mills, K.; Smiths, G. F. Heterocyclic Chemistry, 3rd ed.; Chapman & Hall: London, U. K., 1972; pp 120-145.
20. (b) Suggs, J. W.; Pearson, G. D. J. Org. Chem. 1980, 45, 1514.
21. (c) Cho, C. S.; Kim, T. K.; Choi, H.-J.; Shim, S. C. Bull. Korean Chem. Soc. 2002, 23, 541.
22. (d) Kim, J. N.; Lee, K. Y.; Ham, H.-S.; Kim, H. R.; Ryu, E. K. Bull. Korean Chem. Soc. 2001, 22, 135.
23. 11NO 197.079594, found 197.079411.
24. +), 182 (100), 168 (25), 156 (16), 154 (34.8), 128 (21.5). Other products, 5, 6, and 7 have already been reported (see ref. 4(a)).
25. Suggs, J. W.; Jun, C.-H. J. Chem. Soc., Chem. Commun. 1985, 92.
26. (a) Mecking, S.; Keim, W. Organometallics 1996, 15, 2650.
27. (b) DiRenzo, G. M.; White, P. S.; Brookhart, M. J. Am. Chem. Soc. 1996, 118, 6225.
28. (a) Tolman, C. A. J. Am. Chem. Soc. 1970, 92, 6785.
29. (b) Bray, K. L. Charmant, J. P. H.; Fairlamb, I. J. S.; Lloyd-Jones, G. C. Chem. Eur J. 2001, 7, 4205.
30. (c) Deckers, P. J. W.; Hessen, B.; Teuben, J. H. Angew. Chem. Int. Ed. 2001, 40, 2516.
31. (d) Cárdenas, D. J.; Alcamí, M. Cossío, F.; Méndez, M.; Echavarren, A. M. Chem. Eur. J. 2003, 9, 96.