Convenient syntheses of a family of easily recoverable fluorous primary, secondary and tertiary aliphatic amines NH(3-x[(CH2)(m)(CF2)7CF3](x) (m = 3-5; x = 1-3) - Fine tuning of basicities and fluorous phase affinities

European Journal of Organic Chemistry

Volumn , Issue 14, 2000, Pages 2621-2628

  Rocaboy, Christian ^a,b   Bauer, Walter ^a   Gladysz, John A ^a,b  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b UNIVERSITY OF UTAH   (United States)

Author keywords

Aminations; Amines; Basicity; Fluorine; Partition coefficients; Reductions

Indexed keywords

ALIPHATIC AMINE; FLUORIDE;

ALKALINITY; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; PARTITION COEFFICIENT; SYNTHESIS;

EID: 0033858780     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200007)2000:14<2621::aid-ejoc2621>3.0.co;2-h     Document Type: Article

References (62)

1. [1a] For an overview, see: The Chemistry of Amino, Nitroso, Nitro, and Related Groups (Supplement F2); (Ed.: S. Patai), Wiley: New York, 1996, and similarly titled earlier volumes in this series (1982, 1968).
2. [1b] For some contemporary directions, see: A. Togni, L. M. Venanzi, Angew. Chem. Int. Ed. Engl. 1994, 33, 497-526; Angew. Chem. 1994, 106, 517-547.
3. [1b] For some contemporary directions, see: A. Togni, L. M. Venanzi, Angew. Chem. Int. Ed. Engl. 1994, 33, 497-526; Angew. Chem. 1994, 106, 517-547.
4. E. C. Blossey, W. T. Ford, in: Comprehensive Polymer Science; (Eds.: G. C. Eastmond, A. Ledwith, S. Russo, Sigwalt, P. Volume), Pergamon: New York, 1989; Vol. 6, Chapter 3.5.
5. [3a] W. Xu, R. Mohan, M. M. Morrissey, Tetrahedron Lett. 1997, 38, 7337-7340.
6. [3b] J. Simpson, D. L. Rathbone, D. C. Billington, Tetrahedron Lett. 1999, 40, 7031-7033.
7. [3c] S. Boisnard, J. Chastanet, J. Zhu, Tetrahedron Lett. 1999, 40, 7469-7472.
8. [3d] See also: Aldrichimica Acta 1998, 31, 47 (advertisement).
9. [4a] S. Goumri-Magnet, O. Guerret, H. Gornitzka, J. B. Cazaux, D. Bigg, F. Palacios, G. Bertrand, J. Org. Chem. 1999, 64, 3741-3744.
10. [4b] F. Palacios, D. Aparicio, J. M. de losSantos, A. Baceiredo, G. Bertrand, Tetrahedron 2000, 56, 663-669.
11. [5a] B. Linclau, A. K. Sing, D. P. Curran, J. Org. Chem. 1999, 64, 2835-2842.
12. [5b] J. C. Hodges, Synlett 1999, 152.
13. M. Benaglia, M. Cinquini, F. Cozzi, Tetrahedron Lett. 1999, 40, 2019-2020.
14. D. P. Curran, Angew. Chem. Int. Ed. 1998, 37, 1174-1196; Angew. Chem. 1998, 110, 1230-1255.
15. D. P. Curran, Angew. Chem. Int. Ed. 1998, 37, 1174-1196; Angew. Chem. 1998, 110, 1230-1255.
16. I. T. Horváth, Acc. Chem. Res. 1998, 31, 641-650.
17. Survey of practical considerations and underlying physical principles: L. P. Barthel-Rosa, Gladysz, J. A. Coord. Chem. Rev. 1999, 190-192, 587-605.
18. Review literature from 1999: [10a] E. deWolf, G. varKoten, B.-J. Deelman, Chem. Soc. Rev. 1999, 28, 37-41.
19. [10b] R. H. Fish, Chem. Eur. J. 1999, 5, 1677-1680.
20. [10c] M. Cavazzini, F. Montanari, G. Pozzi, S. Quici, J. Fluorine Chem. 1999, 94, 183-193.
21. [10d] U. Diederichsen, Nachr. Chem. Tech. Lab. 1999, 47, 805-809.
22. L. J. Alvey, D. Rutherford, J. J. J. Juliette, J. A. Gladysz, J. Org. Chem. 1998, 63, 6302-6308.
23. [12a] L. J. Alvey, R. Meier, T. Soós, P. Bernatis, J. A. Gladysz, Eur. J. Inorg. Chem., in press.
24. [12b] L. J. Alvey, Ph.D dissertation, University of Utah, 1999; Chapter 4.
25. I. T. Horváth, G. Kiss, R. A. Cook, J. E. Bond, P. A. Stevens, J. Rábai, Mozeleski, E. J. J. Am. Chem. Soc. 1998, 120, 3133-3143.
26. [14a] D. Rutherford, J. J. J. Juliette, C. Rocaboy, I. Horváth, J. A. Gladysz, Catalysis Today 1998, 42, 381-389.
27. [14b] J. J. J. Juliette, D. Rutherford, I. T. Horváth, J. A. Gladysz, J. Am. Chem. Soc. 1999, 121, 2696-2704.
28. [14c] L. V. Dinh, J. A. Gladysz, Tetrahedron Lett. 1999, 40, 8995-8998.
29. [15a] M.-A. Guillevic, C. Rocaboy, A. M. Arif, I. T. Horváth, J. A. Gladysz, Organometallics 1998, 17, 707-717.
30. [15b] V. Herrera, P. J. F. deRege, I. T. Horváth, T. L. Husebo, R. P. Hughes, Inorg. Chem. Commun. 1998, 1, 197-199.
31. [15c] C. Li, S. P. Nolan, I. T. Horváth, Organometallics 1998, 17, 452-456.
32. [16a] F. Szönyi, F. Guennouni, A. Cambon, J. Fluorine Chem. 1991, 55, 85-92.
33. [16b] F. Guennouni, F. Szönyi, A. Cambon, Synth. Commun. 1994, 24, 2653-2660.
34. L. E. Kiss, J. Rábai, L. Varga, I. Kövesdi, SYNLETT 1998, 1243-1245.
35. [18a] J.-M. Vincent, A. Rabion, V. K. Yachandra, R. H. Fish, Angew. Chem. Int. Ed. Engl. 1997, 36, 2346-2349; Angew. Chem. 1997, 109, 2438-2440.
36. [18a] J.-M. Vincent, A. Rabion, V. K. Yachandra, R. H. Fish, Angew. Chem. Int. Ed. Engl. 1997, 36, 2346-2349; Angew. Chem. 1997, 109, 2438-2440.
37. [18b] G. Pozzi, M. Cavazzini, S. Quici, S. Fontana, Tetrahedron Lett. 1997, 38, 7605-7608.
38. [18c] F. DeCampo, D. Lastécouères, J.-M. Vincent, J.-B. Verlhac, J. Org. Chem. 1999, 64, 4969-4971.
39. S. Quici, M. Cavazzini, S. Ceragioli, F. Montanari, G. Pozzi, Tetrahedron Lett. 1999, 40, 3647-3650.
40. [20a] H. Uno, Y. Shiraishi, K. Shimokawa, H. Suzuki, Chem. Lett. 1988, 729-732.
41. [20b] A. R. Katritzky, Z. Zhang, M. Qi, Tetrahedron Lett. 1997, 38, 7015-7018.
42. M. Gaensslen, U. Gross, H. Oberhammer, S. Rüdiger, Angew. Chem. Int. Ed. Engl. 1992, 31, 1467-1468; Angew. Chem. 1992, 104, 1525-1526.
43. M. Gaensslen, U. Gross, H. Oberhammer, S. Rüdiger, Angew. Chem. Int. Ed. Engl. 1992, 31, 1467-1468; Angew. Chem. 1992, 104, 1525-1526.
44. A. F. Abdel-Magid, K. G. Carson, B. D. Harris, C. A. Maryanoff, R. D. Shah, J. Org. Chem. 1996, 61, 3849-3862, and extensive literature background therein.
45. J. O. Metzger, R. Mahler, A. Schmidt, Liebigs Ann. 1996, 693-696.
46. L. Lévêque, LeM. Blanc, R. Pastor, Tetrahedron Lett. 1998, 39, 8857-8860.
47. [25a] D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277-7287.
48. [25b] M. Frigerio, M. Santagostino, S. Sputore, J. Org. Chem. 1999, 64, 4537-4538.
49. C. Rocaboy, D. Rutherford, B. L. Bennett, J. A. Gladysz, J. Phys. Org. Chem. 2000, 13, in press.
50. Lange's Handbook of Chemistry; 13th Edition, (Ed.: J. A. Dean), McGraw-Hill: New York, 1985; Section 5, Tables 5-8.
51. a determinations, see: [28a] D. L. Holmes, D. A. Lightner, Tetrahedron 1996, 52, 5319-5338.
52. S. Braun, H.-O. Kalinowski, S. Berger, 150 and More Basic NMR Experiments; Wiley-VCH: New York, 1996; pp 279-281.
53. I. Huc, R. Oda, Chem. Commun. 1999, 2025-2026, and references therein.
54. [30a] K. Uneyama, K. Kitagawa, Tetrahedron Lett. 1991, 32, 3385-3386.
55. [30b] Laurent,h. PH. Blancou, A. Commeyras, Tetrahedron Lett. 1992, 33, 2489-2492.
56. [30c] X.-Q. Tang, C.-M. Hu, J. Chem. Soc, Perkin Trans, 1 1994, 2161-2163.
57. M. Schlosser, Angew. Chem. Int. Ed. 1998, 37, 1496-1513; Angew. Chem. 1998, 110, 1538-1556.
58. M. Schlosser, Angew. Chem. Int. Ed. 1998, 37, 1496-1513; Angew. Chem. 1998, 110, 1538-1556.
59. C. Rocaboy, J. A. Gladysz, manuscript in preparation.
60. 3 (δ = 0.00).
61. H. K. Cammenga, M. Epple, Angew. Chem. Int. Ed. Engl. 1995, 34, 1171-1187; Angew. Chem. 1995, 107, 1284-1301.
62. H. K. Cammenga, M. Epple, Angew. Chem. Int. Ed. Engl. 1995, 34, 1171-1187; Angew. Chem. 1995, 107, 1284-1301.