Synthesis of cyclopentadienylmanganese tricarbonyl resins as potential olefin traceless supports

Tetrahedron Letters

Volumn 43, Issue 41, 2002, Pages 7357-7360

  Zhang, Zongren ^a   Lepore, Salvatore D ^a  

^a FLORIDA ATLANTIC UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMIDE; CARBONYL DERIVATIVE; CYMANTRENE; LIGAND; OXIDIZING AGENT; POLYMER; RESIN; UNCLASSIFIED DRUG;

ARTICLE; SPECTROSCOPY; SYNTHESIS;

EID: 0037037847     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01726-4     Document Type: Article

References (18)

1. For recent examples of solid phase olefin synthesis, see: (a) Blaskovich, M. A.; Kahn, M. J. Org. Chem. 1998, 63, 1119; (b) Piscopio, A. D.; Miller, J. F.; Koch, K. Tetrahedron Lett. 1997, 38, 7143.
2. For recent examples of solid phase olefin synthesis, see: (a) Blaskovich, M. A.; Kahn, M. J. Org. Chem. 1998, 63, 1119; (b) Piscopio, A. D.; Miller, J. F.; Koch, K. Tetrahedron Lett. 1997, 38, 7143.
3. 6-linkers involving chromium complexes for the synthesis of benzene derivatives has been reported: (a) Gibson, S. E.; Hales, N. J.; Peplow, M. A. Tetrahedron Lett. 1999, 40, 1417; (b) Semmelhack, M. F.; Hilt, G.; Colley, J. H. Tetrahedron Lett. 1998, 39, 7683.
4. 6-linkers involving chromium complexes for the synthesis of benzene derivatives has been reported: (a) Gibson, S. E.; Hales, N. J.; Peplow, M. A. Tetrahedron Lett. 1999, 40, 1417; (b) Semmelhack, M. F.; Hilt, G.; Colley, J. H. Tetrahedron Lett. 1998, 39, 7683.
5. Coates G.E. Organo-Metallic Compounds. 1960;John Wiley & Sons, Now York.
6. Schinzer D., Blume T., Woltering M. Synlett. 1994;1045.
7. Nesmeyanov A.N., Anisimov K.N., Kolobova N.E., Makarov Y.V. Izv. Akad. Nauk SSSR, Ser. Khim. 3:1968;686.
8. Herberhold M., Biersack M. J. Organomet. Chem. 503:1995;277.
9. 1H NMR and IR.
10. 3).
11. 2 and MeOH successively. It was then dried in vacuo to give cymantrene resin 5 in 98% loading yield (1.0 mmol/g).
12. Booth R.J., Hodges J.C. J. Am. Chem. Soc. 119:1997;4882.
13. 2 and THF successively, and dried in vacuo to give a yellow-colored cymantrene resin in 84% loading yield (0.94 mmol/g).
14. Yan B., Kumaravel G., Anjaria H., Wu A., Petter R.C., Jewell C.F., Wareing J.R. J. Org. Chem. 60:1995;5736.
15. Adams D.M., Squire A. J. Organomet. Chem. 63:1973;381.
16. We found that the light-mediated CO-THF exchange of cymantrene can be executed in common glassware using a low-watt UV (365 nm) lamp. The reaction process can be monitored by the appearance of a deep-red color. Using a UV-vis spectrometer, we determined that the red color reached its greatest intensity after 30 min of irradiation in our setup.
17. 2) decomposes upon extended air exposure especially when in solution.
18. 2O over the course of 25 min.