Benzocycloheptynedicobalt complexes by intramolecular Nicholas reactions

Synlett

Volumn , Issue 2, 2005, Pages 271-274

  Ding, Yu ^a   Green, James R ^a  

^a UNIVERSITY OF WINDSOR   (Canada)

Author keywords

Alkynes; Arenes; Complexes; Nicholas reactions; Transition metals

Indexed keywords

ACETIC ACID DERIVATIVE; BENZOCYCLOHEPTYNEDICOBALT COMPLEX; BENZOCYLOHEPTENYNE DICOBALT COMPLEX; COBALT COMPLEX; HETEROCYCLIC COMPOUND; LEWIS ACID; PROPARGYL ACETATE DICOBALT COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; BINDING KINETICS; BINDING SITE; CHEMICAL INTERACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION; METAL BINDING; NICHOLAS REACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 13944261199     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-837215     Document Type: Article

References (31)

1. For recent reviews, see: (a) Green, J. R. Curr. Org. Chem. 2001, 5, 809.
2. (b) Teobald, B. J. Tetrahedron 2002, 58, 4133.
3. (a) Lu, Y.; Green, J. R. Synlett 2001, 243.
4. (b) Patel, M. M.; Green, J. R. Chem. Commun. 1999, 509.
5. Green, J. R. Chem. Commun. 1998, 1751.
6. (a) Tanino, K.; Onuki, K.; Asano, K.; Miyashita, M.; Nakamura, T.; Takahashi, Y.; Kuwajima, I. J. Am. Chem. Soc. 2003, 125, 1498.
7. (b) Tanino, K.; Kondo, F.; Shimizu, T.; Miyashita, M. Org. Lett. 2002, 4, 2217.
8. Tanino, K.; Shimizu, T.; Miyama, M.; Kuwajima, I. J. Am. Chem. Soc. 2000, 122, 6116.
9. Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128.
10. (a) Young, D. G. J.; Burlison, J. A.; Peters, U. J. Org. Chem. 2003, 68, 3494.
11. (b) Green, J. R. Synlett 2001, 353.
12. Iwasawa, N.; Sakurada, F.; Iwamoto, M. Org. Lett. 2000, 2, 871.
13. Iwasawa, N.; Satoh, H. J. Am. Chem. Soc. 1999, 121, 7951.
14. For examples, see: (a) Uchiyama, N.; Kiuchi, F.; Ito, M.; Honda, G.; Takeda, Y.; Khodzhimatov, O. K.; Ashurmetov, O. A. J. Nat. Prod. 2003, 66, 128.
15. (b) Ulubelen, A.; Topcu, G. J. Nat. Prod. 2000, 63, 879.
16. For examples, see: (a) Ulubelen, A.; Topcu, G.; Tan, N.; Lin, L.-J.; Cordell, G. A. Phytochemistry 1992, 31, 2419.
17. (b) Purushothaman, K. K.; Chandrasekharan, S.; Cameron, A. F.; Connolly, J. D.; Labbe, C.; Maltz, A.; Rycroft, D. S. Tetrahedron Lett. 1979, 979.
18. Lee, J.; Hong, J. J. Org. Chem. 2004, 69, 6433.
19. Bentley, K. W. Nat. Prod. Rep. 2004, 21, 395; and references therein.
20. For examples, see: (a) Ho, T.-L.; Lin, Y.-J. J. Chem. Soc., Perkin Trans. 1 1999, 1207.
21. (b) Inoue, M.; Carson, M. W.; Frontier, A. J.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 1878.
22. Asakawa, Y.; Toyota, M.; Tsunematsu, T.; Kubo, L; Nakanishi, K. Phytochemistry 1980, 19, 2147.
23. Ramirez, F.; Desai, N. B.; McKelvie, N. J. Am. Chem. Soc. 1962, 84, 1745.
24. Uenishi, J.; Kawahama, R.; Yonemitsu, O.; Tsuji, J. J. Org. Chem. 1996, 63, 8965.
25. 8OS: 164.0296; found: 164.0292.
26. Abstract.
27. 3 solution was added, and the mixture was subjected to a conventional work up. Purification by flash chromatography afforded sequentially the benzocycloheptenyne complex and any recovered starting material.
28. This reflects a tendency for a slightly lower preference for C-2 reactivity in thiophenes relative to furans and perhaps the known tendency for electron withdrawing C-3 groups to deactivate C-2 to a greater degree than C-4. See: Taylor, R. In The Chemistry of Heterocyclic Compounds, Part 2, Vol. 44; Gronowitz, S., Ed.; Wiley. New York, 1986, Chap. 1, 16.
29. Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; Wiley and Sons: New York, 2000.
30. Abstract.
31. Hosokawa, S.; Isobe, M. Tetrahedron Lett. 1998, 39, 2609.