A novel strategy for the synthesis of ω-functionalized perfluoroalkyl iodides

Organic Letters

Volumn 3, Issue 15, 2001, Pages 2365-2366

  Szlávik, Zoltán ^a   Tárkányi, Gábor ^a,b   Skribanek, Zsolt ^a,b   Vass, Elemér ^a   Rábai, József ^a  

^a EÖTVÖS LORÁND UNIVERSITY   (Hungary)

^b GEDEON RICHTER LTD   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001354919     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0161662     Document Type: Article

References (33)

1. (a) Horváth, I. T.; Rábai, J. Science 1994, 266, 72.
2. (b) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641.
3. (c) Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. J. Fluorine Chem. 1999, 94, 183.
4. (d) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37.
5. (e) Fish, R. D. Chem. Eur. J. 1999, 5, 1677.
6. (f) Yeung, L. K.; Crooks, R. M. Nano Lett. 2001, 1, 14.
7. (a) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531.
8. (b) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823.
9. (c) Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1175.
10. (d) Curran, D. P.; Luo, Z. J. Am. Chem. Soc. 1999, 121, 9069.
11. (e) Luo, Z.; Zhang, Q.; Oderaotoshi, Y.; Curran, D. P. Science 2001, 291, 1766.
12. (a) Herrera, V.; de Rege, P. J. F.; Horváth, I. T.; Husebo, T. L.; Hughes, R. P. Inorg. Chem. Commun. 1998, 1, 197.
13. (b) Barthel-Rosa, L. P.; Gladysz, J. A. Coord. Chem. Rev. 1999, 190-192, 587.
14. (c) Rocaboy, C.; Rutherford, D.; Bennett, B. L.; Gladysz, J. A. J. Phys. Org. Chem. 2000, 13, 596.
15. For calculation of "fluorousness" from partition data, see: (d) Kiss, L. E.; Kövesdi, I.; Rábai, J. J. Fluorine Chem. 2001, 108, 95.
16. Deev, L. E.; Nazarenko, T. I.; Pashkevich, K. I.; Ponomarev, V. G. Russ. Chem. Rev. 1992, 61, 40.
17. Pensec, S.; Tournilhac, F. G.; Bassoul, P.; Durliat, C. J. Phys. Chem. B 1998, 102, 52.
18. Mougenot, P.; Mertens, P.; Nguyen, M.; Touillaux, R.; Marchand-Brynaert, J. J. Org. Chem. 1996, 61, 408.
19. Sun, F.; Castner, D. G.; Mao, G.; Wang, W.; McKeown, P.; Grainger, D. W. J. Am. Chem. Soc. 1996, 118, 1856.
20. Szlávik, Z.; Csámpai, A.; Krafft, M. P.; Riess, J. G.; Rábai, J. Tetrahedron Lett. 1997, 38, 8757.
21. Szlávik, Z.; Tárkányi, G.; Gömöry, Á.; Rábai, J. Org. Lett. 2000, 2, 2347.
22. Selected examples: (a) R = Cl. Chen, Q.-Y.; Su, D.-B.; Yang, Z. Y.; Zhu, R.-X. J. Fluorine Chem. 1987, 36, 483.
23. (b) R = Br. Brace, N. O. U.S. Pat. 3145222, 1961; Chem. Abstr. 1964, 61, 10589g.
24. (c) R = COCl. McLaughlin, V. C. R. Tetrahedron Lett. 1968, 4761.
25. 2H. Huang, W.-Y.; Huang, B.-N.; Hu, C.-M. J. Fluorine Chem. 1983, 23, 229.
26. 2Cl. Qiu, W.; Burton, D. J. J. Fluorine Chem. 1993, 62, 273.
27. Nguyen, T.; Rubinstein, M.; Wakselman, C. Synth. Commun. 1983, 13, 81.
28. 4 and the solvent was removed by rotary evaporation. The residue was distilled under reduced pressure (170-180°C bath temperature, approximately 20 mmHg) to yield 2 (3.13 g, 86%); (Z):(E) = 3.3:1 (determined by GC and NMR).
29. Moiseeva, N. I.; Gekhman, A. E.; Rumyantsev, E. S.; Klimanov, V. I.; Moiseev, I. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1989, 1706; Chem. Abstr. 1990, 112, 76130.
30. Moiseeva, N. I.; Gekhman, A. E.; Rumyantsev, E. S.; Klimanov, V. I.; Moiseev, I. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1989, 1706; Chem. Abstr. 1990, 112, 76130.
31. Odinokov, V. N.; Akhmetova, V. R.; Savchenko, R. G.; Bazunova, M. V.; Fatykhov, A. A.; Zapevalov, A. Y. Izv. Akad. Nauk., Ser. Khim. 1997, 1239; Chem. Abstr. 1998, 128, 22618.
32. Odinokov, V. N.; Akhmetova, V. R.; Savchenko, R. G.; Bazunova, M. V.; Fatykhov, A. A.; Zapevalov, A. Y. Izv. Akad. Nauk., Ser. Khim. 1997, 1239; Chem. Abstr. 1998, 128, 22618.
33. 2 to remove ozone residues. Complete reaction was observed by GC. The solvent was regenerated using atmospheric distillation (70 mL, 99.4% GC purity). The residue was distilled at reduced pressure in a short path apparatus (85-100°C bath temperature/0.1 mmHg) to afford 3b (8.47 g, 93%, 92% purity by GC).