Reverse fluorous solid-phase extraction: A new technique for rapid separation of fluorous compounds

Organic Letters

Volumn 6, Issue 16, 2004, Pages 2717-2720

  Matsugi, Masato ^a   Curran, Dennis P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORIDE;

ARTICLE; LIQUID LIQUID EXTRACTION; PHASE SEPARATION; SEPARATION TECHNIQUE; SOLID PHASE EXTRACTION; SOLID STATE;

CHROMATOGRAPHY, GEL; FLUORINE COMPOUNDS; ORGANIC CHEMICALS; SILICON DIOXIDE; SOLVENTS;

EID: 4344641834     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049040o     Document Type: Article

References (27)

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15. 254 (MERCK); and α-cellulose, AVICEL F Macrocrystalline Cellulose (ANALTECH).
16. 3.
17. f is the chromatographic retention factor, and Rf is a perfluoroalkyl group.
18. f values in 100% hexane were variable, possibly due to the water content of the silica gel. However, the relative polarities were not variable.
19. Ryu, I.; Kreimerman, S.; Niguma, T.; Minakata, S.; Komatsu, M.; Luo, Z.; Curran, D. P. Tetrahedron Lett. 2001, 42, 947-950.
20. 2O (2/1) to give 3-(perfluorodecyl)prop-1-ene in 97% yield (271 mg).
21. Purity of the products was determined by GC in the case of R = H or R = Me and HPLC (Nova Pak Silica, UV detection at 254 nm) in the case of R = Ph.
22. Naji, N.; Soufiaoui, M.; Moreau, P. J. Fluorine Chem. 1996, 79, 179-183.
23. Mukaiyama, T.; Matsueda, R.; Suzuki, M. Tetrahedron Lett. 1970, 22, 1901-1904.
24. Luo, Z.; Williams, J.; Read, R. W.; Curran, D. P. J. Org. Chem. 2001, 66, 4261-4266.
25. Tabuchi, S.; Itani, H.; Sakata, Y.; Oohashi, H.; Satoh, Y. Biol. Med. Chem. Lett. 2002, 12, 1171-1175.
26. Purity of the products was determined by HPLC (Nova Pak Silica) with UV detection at 254 nm.
27. Other readily available fluorous solvents can be used in place of FC-72; see ref 2c. FC-72 can be recovered from FC-72/ether mixtures by simple distillation; the fraction boiling at 54-57°C was collected and reused.