Facile synthesis of novel bis- and tetrakis(2-ferrocenylvinyl)[2.2]paracyclophanes by palladium-catalyzed coupling reactions

Synthesis

Volumn , Issue 1, 1997, Pages 35-37

  Kay, Kwang Yol ^a   Baek, Yong Gu ^a   Han, Dae Won ^a   Yeu, Sang Yong ^a  

^a Ajou University   (South Korea)

Author keywords

mono , bis , tetrakis (2 ferrocenylvinyl) 2.2 paracyclophanes; palladium catalyzed coupling; vinylferrocene

Indexed keywords

FERROCENE DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SPECTROPHOTOMETRY; STEREOCHEMISTRY;

EID: 0031053428     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1506     Document Type: Article

References (23)

1. Long, N.J. Angew. Chem. 1995, 107, 37; Angew. Chem., Int. Ed. Engl. 1995, 34, 21, and references therein. Green, M.L.H.; Marder, S.R.; Thompson, M.E.; Bandy, J.A.; Bloor, D.; Kolinsky, P.V.; Jones, R.J. Nature 1987, 330, 360. Eaton, D.F. Science 1991, 281. Calabrese, J.C.; Cheng, L.-T.; Green, J.C.; Marder, S.R.; Tam, W. J. Am Chem. Soc. 1991, 113, 7227. Marder, S.R.; Perry, J.W.; Tiemann, B.G.; Schaefer, W.P. Organometallics 1991, 10, 1896.
2. Long, N.J. Angew. Chem. 1995, 107, 37; Angew. Chem., Int. Ed. Engl. 1995, 34, 21, and references therein. Green, M.L.H.; Marder, S.R.; Thompson, M.E.; Bandy, J.A.; Bloor, D.; Kolinsky, P.V.; Jones, R.J. Nature 1987, 330, 360. Eaton, D.F. Science 1991, 281. Calabrese, J.C.; Cheng, L.-T.; Green, J.C.; Marder, S.R.; Tam, W. J. Am Chem. Soc. 1991, 113, 7227. Marder, S.R.; Perry, J.W.; Tiemann, B.G.; Schaefer, W.P. Organometallics 1991, 10, 1896.
3. Long, N.J. Angew. Chem. 1995, 107, 37; Angew. Chem., Int. Ed. Engl. 1995, 34, 21, and references therein. Green, M.L.H.; Marder, S.R.; Thompson, M.E.; Bandy, J.A.; Bloor, D.; Kolinsky, P.V.; Jones, R.J. Nature 1987, 330, 360. Eaton, D.F. Science 1991, 281. Calabrese, J.C.; Cheng, L.-T.; Green, J.C.; Marder, S.R.; Tam, W. J. Am Chem. Soc. 1991, 113, 7227. Marder, S.R.; Perry, J.W.; Tiemann, B.G.; Schaefer, W.P. Organometallics 1991, 10, 1896.
4. Long, N.J. Angew. Chem. 1995, 107, 37; Angew. Chem., Int. Ed. Engl. 1995, 34, 21, and references therein. Green, M.L.H.; Marder, S.R.; Thompson, M.E.; Bandy, J.A.; Bloor, D.; Kolinsky, P.V.; Jones, R.J. Nature 1987, 330, 360. Eaton, D.F. Science 1991, 281. Calabrese, J.C.; Cheng, L.-T.; Green, J.C.; Marder, S.R.; Tam, W. J. Am Chem. Soc. 1991, 113, 7227. Marder, S.R.; Perry, J.W.; Tiemann, B.G.; Schaefer, W.P. Organometallics 1991, 10, 1896.
5. Long, N.J. Angew. Chem. 1995, 107, 37; Angew. Chem., Int. Ed. Engl. 1995, 34, 21, and references therein. Green, M.L.H.; Marder, S.R.; Thompson, M.E.; Bandy, J.A.; Bloor, D.; Kolinsky, P.V.; Jones, R.J. Nature 1987, 330, 360. Eaton, D.F. Science 1991, 281. Calabrese, J.C.; Cheng, L.-T.; Green, J.C.; Marder, S.R.; Tam, W. J. Am Chem. Soc. 1991, 113, 7227. Marder, S.R.; Perry, J.W.; Tiemann, B.G.; Schaefer, W.P. Organometallics 1991, 10, 1896.
6. Long, N.J. Angew. Chem. 1995, 107, 37; Angew. Chem., Int. Ed. Engl. 1995, 34, 21, and references therein. Green, M.L.H.; Marder, S.R.; Thompson, M.E.; Bandy, J.A.; Bloor, D.; Kolinsky, P.V.; Jones, R.J. Nature 1987, 330, 360. Eaton, D.F. Science 1991, 281. Calabrese, J.C.; Cheng, L.-T.; Green, J.C.; Marder, S.R.; Tam, W. J. Am Chem. Soc. 1991, 113, 7227. Marder, S.R.; Perry, J.W.; Tiemann, B.G.; Schaefer, W.P. Organometallics 1991, 10, 1896.
7. Nicoud, J.F.; Twieg, R.J. In Nonlinear Optical Properties of Organic Molecules and Crystals; Chemia, D.S.; Zyss, J., Eds.; Academic: New York, 1987, Chapter 11-3.
8. Ghosal, S.; Samoc, M.; Prasad, P.N.; Tufariello, J.J. J. Phys. Chem. 1990, 94, 2847.
9. Cyclophanes I and II; Keehn, P.M.; Rosenfeld, S.M., Eds.; Academic: New York, 1983. Vögtle, F. Cyclophane Chemistry; Wiley: New York, 1993.
10. Cyclophanes I and II; Keehn, P.M.; Rosenfeld, S.M., Eds.; Academic: New York, 1983. Vögtle, F. Cyclophane Chemistry; Wiley: New York, 1993.
11. Heck, R.F. Palladium Reagents in Organic synthesis; Academic: London, 1985.
12. McMurry, J.E.; Fleming, M.P. J. Am. Chem. Soc. 1974, 96, 4708. Lenoir, D. Synthesis 1977, 553.
13. McMurry, J.E.; Fleming, M.P. J. Am. Chem. Soc. 1974, 96, 4708. Lenoir, D. Synthesis 1977, 553.
14. El-Tamany, S.; Raulfs, F.-W.; Hopf, H. Angew. Chem. 1983, 95, 631; Angew. Chem., Int. Engl. 1983, 22, 633.
15. El-Tamany, S.; Raulfs, F.-W.; Hopf, H. Angew. Chem. 1983, 95, 631; Angew. Chem., Int. Engl. 1983, 22, 633.
16. Jeffery, T. Tetrahedron Lett. 1985, 26, 2667. Jeffery, T. Tetrahedron Lett. 1990, 31, 6641.
17. Jeffery, T. Tetrahedron Lett. 1985, 26, 2667. Jeffery, T. Tetrahedron Lett. 1990, 31, 6641.
18. Staab, H.A.; Wahl, P.; Kay, K.-Y. Chem. Ber. 1987, 120, 541.
19. Reich, H.J.; Cram, D.J. J. Am. Chem. Soc. 1969, 91, 3534.
20. Henkel and Cie GmbH, Brit. Patent 807720, 1959; Chem. Abstr. 1960, 54, 412g.
21. Gray, R.; Boekelheide, V. J. Am. Chem. Soc. 1979, 101, 2128.
22. Dubeck, M.; Brackenridge, D.R., U.S. Patent 3899466, 1975; Chem. Abstr. 1975, 83, 207105x.
23. Ruggli, P.; Bussemaker, B.B.; Müller, W. Helv. Chim. Acta 1935, 18, 613.