Fluorinated analogues of tert-butyl alcohol as novel protecting groups for use in fluorous synthesis

Organic Letters

Volumn 3, Issue 23, 2001, Pages 3711-3714

  Pardo, Juan ^a   Cobas, Agustín ^a   Guitián, Enrique ^a   Castedo, Luis ^a  

^a Facultade de Ciencias   (Spain)

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EID: 0000245903     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0166505     Document Type: Article

References (39)

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29. See refs 6a and 5a for the preparation of Grignard 1 and 4.
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31. See for example: (a) Maul, J. J.; Ostrowski, P. J.; Ublacker, G. A.; Linclau, B.; Curran, D. P. Benzotrifluoride and Derivatives: Useful Solvent for Organic Synthesis and Fluorous Synthesis. In: Topics in Current Chemistry, Modern Solvents in Organic Synthesis; Knochel, P., Ed.; Springer-Verlag: Berlin-Heidelberg, 1999; Vol. 206, p 79.
32. (b) Colonma, S.; Gaggero, N.; Montanari, F.; Pozzi, G.; Quici, S. Eur. J. Org. Chem. 2001, 181-186.
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34. D = C(fluorous phase)/C(organic phase), at 25°C.
35. The partition coefficients were determined by dissolving a known amount of the fluorous compound (40-70 mg) in the biphasic system (4 mL, 1:1 v/v). The resulting mixture was vigorously stirred for 15 min in a 10 mL vial, immersed in a 25°C oil bath. After two clear layers were obtained, a 1 mL aliquot was removed from each layer with a syringe. This was evaporated to dryness, and the weight (± 0.1 mg) of each residue was determined. The partition coefficients were calculated as the ratio of the amount of residue from each layer.
36. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's, Textbook of Practical Organic Chemistry, 5th ed.; ELBS: London, 1989.
37. Polar compounds need a larger percentage of fluor than nonpolar compounds to be soluble in fluorous solvent because the fluorous solvents keep some nonpolar character (Guillevic, M. A.; Rocaboy, C.; Arif, A. M.; Horvath, I. T.; Gladysz, J. A. Organometallics 1998, 17, 707-717. Also, ref 7). For polar compounds it will be necessary to increase the length of the pony tails of the alcohol to get adequate fluorous solubility and affinity. Otherwise other nobel fluorous techniques referred to as light fluorous techniques, allow the separation of fluorous compounds readily without increasing the length of the pony tails. See ref 9c and (a) Zhang, Q.; Luo, Z.; Curran, D. P. J. Org. Chem. 2000, 65, 8866-8876.
38. Polar compounds need a larger percentage of fluor than nonpolar compounds to be soluble in fluorous solvent because the fluorous solvents keep some nonpolar character (Guillevic, M. A.; Rocaboy, C.; Arif, A. M.; Horvath, I. T.; Gladysz, J. A. Organometallics 1998, 17, 707-717. Also, ref 7). For polar compounds it will be necessary to increase the length of the pony tails of the alcohol to get adequate fluorous solubility and affinity. Otherwise other nobel fluorous techniques referred to as light fluorous techniques, allow the separation of fluorous compounds readily without increasing the length of the pony tails. See ref 9c and (a) Zhang, Q.; Luo, Z.; Curran, D. P. J. Org. Chem. 2000, 65, 8866-8876.
39. (b) Luo, Z.; Zhang, Q.; Oderaotoshi, Y.; Curran, D. P. Science 2001, 291, 1766-1769 and references therein.