Regiocontrolled Synthesis of CpCo-Cyclobutadienyl-Bridged p-Cyclophanes via Annulation of Acyclic Diynes

Journal of Organic Chemistry

Volumn 62, Issue 20, 1997, Pages 6708-6709

  Brisbois, Ronald G ^a   Fogel, Louis E ^a   Nicaise, Olivier J C ^a   DeWeerd, Peter J ^a  

^a HAMLINE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001736771     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971022f     Document Type: Article

References (31)

1. (a) Host-Guest Chemistry; Vögtle, F., Weber, E., Eds.; Springer-Verlag: Berlin, 1985.
2. (b) Cyclophanes; Diederich, F.; CRC Press, Inc.: Boca Raton, FL, 1991.
3. (c) Calixarenes; Gutsche, C. D.; CRC Press, Inc.: Boca Raton, FL, 1989.
4. (a) Burley, S. K.; Petsko, G. A. Adv. Protein Chem. 1988, 39, 125.
5. (b) Serrano, L.; Bycroft, M.; Fersht, A. R. J. Mol. Biol. 1991, 218, 465.
6. (a) Brisbois, R. G.; Wanke, R. A.; Burns, S. J.; Rappath, D. W. Unpublished results.
7. (b) Asami, M.; Krieger, C.; Staab, H. A. Tetrahedron Lett. 1991, 32, 2117.
8. (a) Cyclophanes; Keehn, P. M., Rosenfeld, S. M., Eds.; Academic Press: New York, 1983; Vols. I and II.
9. (b) Cyclophanes I and Cyclophanes II; Vögtle, F., Ed.; Topics in Current Chemistry 113 and 115; Springer-Verlag: Berlin, 1983.
10. (b) Cyclophanes I and Cyclophanes II; Vögtle, F., Ed.; Topics in Current Chemistry 113 and 115; Springer-Verlag: Berlin, 1983.
11. Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539.
12. For an example of successful closure of a medium/large ring via Co-mediated [2 + 2 + 2] aromatic annulation, see: Lofthagen, M.; Chadha, R.; Siegel, J. S. J. Am. Chem. Soc. 1991, 113, 8785.
13. (a) Rausch, M. D.; Genetti, R. A. J. Org. Chem. 1970, 35, 3888.
14. (b) Hillard, R. L., III; Vollhardt, K. P. C. J. Am. Chem. Soc. 1977, 99, 4058.
15. (c) Efraty, A. Chem. Rev. 1977, 77, 691.
16. (a) Gleiter, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 27 and references cited therein.
17. (b) Gleiter, R.,' Merger, R.; Nuber, B. J. Am. Chem. Soc. 1992, 114, 8921.
18. (c) Gleiter, R.; Merger, R.; Irngartinger, H.; Nuber, B. J. Org. Chem. 1993, 58, 2025.
19. (d) Gleiter, R.; Langer, H.; Nuber, B. Angew. Chem., Int. Ed. Engl. 1994, 33, 1272.
20. (e) Gleiter, R.; Langer, H.; Schehlmann, V.; Nuber, B. Organometallics 1995, 14, 975.
21. (f) Gleiter, R.; Stahr, H.; Nuber, B. Tetrahedron Lett. 1995, 36, 4607.
22. The authors have deposited atomic coordinates for structures depicted in Figure 1 with the Cambridge Cystallographic Data Centre. The coordinates can be obtained, upon request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
23. A number of cobaltacyclopentadienes have been isolated and characterized. (a) McAlister, D. R.; Bercaw, J. E.; Bergman, R. G. J. Am. Chem. Soc. 1977, 99, 1666. (b) McDonnell Bushnell, L. P.; Evitt, E. R.; Bergman, R. G. J. Organomet. Chem. 1978, 157, 445. (c) Yamazaki, H.; Wakatsuki, Y. J. Organomet. Chem. 1977, 139, 157. (d) Yamazaki, H.; Wakatsuki, Y. J. Am. Chem. Soc. 1980, 102, 4363.
24. A number of cobaltacyclopentadienes have been isolated and characterized. (a) McAlister, D. R.; Bercaw, J. E.; Bergman, R. G. J. Am. Chem. Soc. 1977, 99, 1666. (b) McDonnell Bushnell, L. P.; Evitt, E. R.; Bergman, R. G. J. Organomet. Chem. 1978, 157, 445. (c) Yamazaki, H.; Wakatsuki, Y. J. Organomet. Chem. 1977, 139, 157. (d) Yamazaki, H.; Wakatsuki, Y. J. Am. Chem. Soc. 1980, 102, 4363.
25. A number of cobaltacyclopentadienes have been isolated and characterized. (a) McAlister, D. R.; Bercaw, J. E.; Bergman, R. G. J. Am. Chem. Soc. 1977, 99, 1666. (b) McDonnell Bushnell, L. P.; Evitt, E. R.; Bergman, R. G. J. Organomet. Chem. 1978, 157, 445. (c) Yamazaki, H.; Wakatsuki, Y. J. Organomet. Chem. 1977, 139, 157. (d) Yamazaki, H.; Wakatsuki, Y. J. Am. Chem. Soc. 1980, 102, 4363.
26. A number of cobaltacyclopentadienes have been isolated and characterized. (a) McAlister, D. R.; Bercaw, J. E.; Bergman, R. G. J. Am. Chem. Soc. 1977, 99, 1666. (b) McDonnell Bushnell, L. P.; Evitt, E. R.; Bergman, R. G. J. Organomet. Chem. 1978, 157, 445. (c) Yamazaki, H.; Wakatsuki, Y. J. Organomet. Chem. 1977, 139, 157. (d) Yamazaki, H.; Wakatsuki, Y. J. Am. Chem. Soc. 1980, 102, 4363.
27. a ≈ 28) provides an example which can be used to advantage in enolate generation. See: Brown, C. A. J. Org. Chem. 1974, 39, 3913. Danheiser, R. L.; Miller, R. F.; Brisbois, R. G; Park, S. Z. J. Org. Chem. 1990, 55, 1959 and references cited therein.
28. a ≈ 28) provides an example which can be used to advantage in enolate generation. See: Brown, C. A. J. Org. Chem. 1974, 39, 3913. Danheiser, R. L.; Miller, R. F.; Brisbois, R. G; Park, S. Z. J. Org. Chem. 1990, 55, 1959 and references cited therein.
29. (b) Colvin, E. Silicon in Organic Synthesis; Springer-Verlag: Berlin, 1983.
30. (a) Mao, S. S. H.; Tilley, T. D. J. Am. Chem. Soc. 1995, 117, 5365.
31. (b) Mao, S. S. H.; Tilley, T. D. J. Am. Chem. Soc. 1995, 117, 7031.