3928
I. Kani et al. / Tetrahedron 58 72002) 3923±3928
after vacuum drying .75% yield). 31P NMR .121 MHz,
external chloroform-d lock) d 216.5; 29.6 and 66.9 broad
formylation in Supercritical Carbon Dioxide Using Rhodium-
based Catalyst With Fluorinated Ligands, in preparation.
Â
18. Juliette, J. J. J.; Horvath, I. T.; Gladysz, J. A. Angew. Chem.,
peak.
Elemental
analysis:
calc.
for
Int. Ed. Engl. 1977, 36, 1610.
19. Guillievic, M. A.; Arif, A. M.; Horvath, I. T.; Gladysz, J. A.
C834H480O123F1020N3P3Cl1Rh1: C, 31.17; H, 1.49; O, 6.13;
N, 0.13; P, 0.29; Rh, 0.32. Found: C, 30.83; H, 1.35; O,
5.90; N, 0.20; P, 0.20; Rh, 0.24.
Â
Angew. Chem., Int. Ed. Engl. 1997, 36, 2466.
20. .a) Kaintz, S.; Koch, D.; Bauman, W.; Leitner, W. Angew.
Chem., Int. Ed. Engl. 1997, 15, 1628±1630. .b) Kaintz, S.;
Brinkmann, A.; Leitner, W.; Pfaltz, A. J. Am. Chem. Soc.
1999, 121, 6421±6429. .c) Hori, H.; Six, C.; Leitner, W.
Macromolecules 1999, 32, 3178±3182. .d) Francio, G.;
Wittmann, K.; Letner, W. J. Organomet. Chem. 2001, 621,
130±142.
Acknowledgements
This work was supported by The Environmental Protection
Agency .EPA), The Scienti®c and Technical Research
Council of Turkey .TUBITAK-NATO), Consejo Nacional
de Ciencia y Tecnologia .CONACYT) and Texas A&M
University. DuPont Company supplied us the necessary
¯uoroacrylate monomer. We thank Professor David
Bergbreiter and his group at Texas A&M University for
very important consultations throughout this project.
Â
Â
21. Horvath, I. T.; Rabai, J. Science 1994, 266, 72±75.
Â
22. Horvath, I. T. Acc. Chem. Res. 1998, 31, 641±650.
Â
23. Juliette, J. J. J.; Rutherford, D.; Horvath, I. T.; Gladysz, J. A.
J. Am. Chem. Soc. 1999, 121, 2696±2704.
24. Fawcette, J.; Hope, E. G.; Kemmitt, R. D. W.; Paige, D. R.;
Russel, D. R.; Shat, A. M.; Cole-Hamilton, D. J.; Pane, M. J.
J. Am. Chem. Soc. 1997, 119, 1127±1128.
25. Pozzi, G.; Colombani, I.; Mialieli, M.; Montonari, F.; Quicki,
S. M. Tetrahedron 1996, 52, 11829±11888.
References
26. Domagno, S. G.; Williams, R. A.; Therien, M. J. J. Org. Chem.
1994, 59, 6943±6948.
1. .a) Mohr, B.; Lynn, D. M.; Grubbs, R. H. Organometallics
1996, 4317±4325. .b) Lynn, D. M.; Mohr, B.; Grubbs, R. H.
J. Am. Chem. Soc. 1998, 120, 1627±1628.
27. Hughes, R. P.; Trujillo, H. A. Organometallics 1996, 15, 280±
284.
Â
28. Horvath, I. I.; Kiss, G.; Cook, R. A.; Bond, J. E.; Stevens,
P. A.; Rabai, J.; Mozoleski, E. J. J. Am. Chem. Soc. 1998,
120, 3233.
Â
Â
2. .a) Horvath, L. T.; Rabai, J. Science 1994, 266, 71±75.
.b) Vincent, J. M.; Rabian, A.; Yachanda, V. K.; Fish, R. H.
Angew. Chem., Int. Ed. Engl. 1997, 36, 2346±2349.
3. Chauvin, Y.; Oliver-Bourbigou, H. Chem. Tech. 1995, 25.9),
26±30.
29. Yazdi, A. V.; Beckman, E. J. Ind. Eng. Chem. Res. 1996, 35,
3644.
30. Dardin, A. E.; DeSimone, J. M.; Samuliki, E. T. J. Phys.
Chem. 1998, 102, 1175.
4. Jessop, P. G.; Leitner, W. Chemical Synthesis Using
Supercritical Fluids; Wiley±VCH: New York, 1999.
5. Geckeler, K. E. Adv. Polym. Sci. 1995, 121, 31±39.
6. Bergbreiter, D. E. Macromol. Symp. 1996, 105, 9±16.
7. Gibertion, S. R.; Wong, X. F.; Hoge, G. S.; Klug, G. A.;
Schaefer, M. J. Organometallics 1996, 15, 4678±4680.
8. Bergbreiter, D. E.; Liu, Y. S. Tetrahedron Lett. 1997, 38,
7843±7846.
31. Koch, D.; Leitner, W. J. Am. Chem. Soc. 1995, 120, 13398.
32. Jessop, P.; Ikaraya, T.; Noyori, R. Organometallics 1995, 14,
1510±1513.
33. Burk, M. J.; Feng, S.; Gross, M. F.; Tumas, W. J. Am. Chem.
Soc. 1995, 2600, 2604.
34. Kainz, S.; Koch, D.; Leitner, M. In Selective Reactions of
Metal Activated Molecules, Werner, H., Schreir, W., Eds.;
Viegweg: Wiesbaden, 1998; pp. 151±156.
9. Bergbreiter, D. E.; Case, B. L.; Liu, Y. S.; Carawey, J. W.
J. Org. Chem. 1998, 63, 6053±6062.
35. Xio, J. L.; Nefkens, S. C. A.; Jessop, P. G.; Ikariya, T.; Noyori,
R. Tetrahedron Lett. 1996, 37, 2813±2816.
36. McHugh, M. A. Macromolecules 1995, 28, 1506.
37. Hsiao, Y. L.; Maury, E. E.; Desimone, J. M.; Mavson, S.;
Jonstan, K. P. Macromolecules 1995, 28, 8159.
38. Yilgor, I.; McGrath, J. E.; Krukonis, V. J. J. Polym. Bull. 1984,
12, 499.
10. Ajgou, A. N.; Alper, H. J. Am. Chem. Soc. 1998, 120, 1466±
1468.
11. Bergbreiter, D. E.; Liu, Y. S. Tetrahedron Lett. 1997, 38,
3703±3706.
12. Jessop, P. G.; Ikariya, T.; Noyori, R. Chem. Rev. 1999, 99,
475±493.
13. Zosel, K. Angew. Chem. 1978, 90, 748.
39. Krukonis, V. J. J. Polym. News 1985, 1, 7.
40. Hoe¯ing, T. A.; Enick, R. M. M.; Beckman, E. J. J. Phys.
Chem. 1991, 95, 7127.
14. Burk, M. J.; Feng, S.; Gross, M. F.; Tumas, W. J. Am. Chem.
Soc. 1995, 8277, 8278.
15. Brookhart, M.; Grant, B.; Volpe Jr., A. F. Organometallics
1992, 11, 3920±3922.
41. Hoe¯ing, T. A.; Stofesky, D.; Reid, M.; Beckman, E. J.;
Enick, R. M. J. Supercrit. Fluids 1992, 5, 237.
42. Bergbreiter, D. E.; Franchina, J. G.; Case, B. L.; Williams,
L. K.; Frels, J. D.; Koshti, N. Comb. Chem. High Througout
Screening 2000, 3, 153±164.
16. .a) Consani, K. A.; Smith, R. D. J. Supercrit. Fluids 1990, 3,
51±56. .b) Dillow, A. K.; Yun, S. L. J.; Suleiman, D.;
Boatright, D. L.; Liotta, L. L.; Eckert, C. A. Ind. Engng.
Chem. Res. 1996, 35, 1801±1806.
43. Bergbreiter, D. E.; Chadron, R. S. J. Am. Chem. Soc. 1987,
109, 174±179.
17. .a) Guzel, B.; Omary, M. A.; Fackler Jr., J. P.; Akgerman, A.
Synthesis and Characterization of {[.COD)Rh.bis-.2R,3R)-
2,5-diethylphospholanobenzene)]BARF} for Use in Homoge-
neous Catalysis in Supercritical Carbon Dioxide. Inorg. Chim.
Acta 2001, 325, 45±50. .b) Lin, B.; Akgerman, A. Ind. Eng.
Chem. Res. 2001, 40, 1113±1118. .c) Lin, B.; Akgerman, A.;
Omary, M. A.; Fackler, J. P., Jr. Kinetics of Styrene Hydro-
44. Bergbreiter, D. E.; Case, B. L.; Liu, Y. S.; Caraway, J. W.
Macromolecules 1998, 31, 6053±6062.
45. Crabtree, R. H.; Giardiona, G. Inorg. Synth. 1979, 19, 218±
220.