Novel generation ponytails in fluorous chemistry: Syntheses of primary, secondary, and tertiary (nonafluoro-tert-butyloxy)ethyl amines

Journal of Fluorine Chemistry

Volumn 127, Issue 11, 2006, Pages 1496-1504

  Szabó, Dénes ^a   Mohl, János ^a   Bálint, Ana Maria ^a   Bodor, Andrea ^a   Rábai, József ^a  

^a EÖTVÖS LORÁND UNIVERSITY   (Hungary)

Author keywords

Amines; Ethers; Fluorous partition coefficient; Steam distillation; Williamson synthesis

Indexed keywords

EID: 33750820706     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2006.06.020     Document Type: Article

References (57)

1. Horváth I.T., and Rábai J. Science 266 (1994) 72-75
2. I.T. Horváth, J. Rábai, US Patent 5,463,082 (Exxon Research and Engineering Co.) October 31, 1995 (application: July 8, 1993); Chem. Abstr. 123 (1995) 87349.
3. Horváth I.T. Acc. Chem. Res. 31 (1998) 641-650
4. Rábai J., Szlávik Z., and Horváth I.T. In: Clark J., and MacQuarrie D. (Eds). Handbook of Green Chemistry and Technology (2002), Blackwell Science, Oxford 502-523 (Chapter 22)
5. In: Gladysz J.A., and Curran D.P. (Eds). Tetrahedron vol. 58 (2002) 3823-4131
6. In: Gladysz J.A., Curran D.P., and Horváth I.T. (Eds). Handbook of Fluorous Chemistry (2004), Wiley/VCH, Weinheim
7. Gladysz J.A. Angew. Chem. Int. Ed. 44 (2005) 5766-5768
8. Freemantle M. Chem. Eng. News 83 (2005) 39-42
9. Horváth I.T., Kiss G., Cook R.A., Bond J.E., Stevens P.A., Rábai J., and Mozeleski E.J. J. Am. Chem. Soc. 120 (1998) 3133-3143
10. Gladysz J.A. In: Gladysz J.A., Curran D.P., and Horváth I.T. (Eds). Handbook of Fluorous Chemistry (2004), Wiley/VCH, Weinheim 41-55 (Chapter 5)
11. Gladysz J.A. In: Gladysz J.A., Curran D.P., and Horváth I.T. (Eds). Handbook of Fluorous Chemistry (2004), Wiley/VCH, Weinheim 24-40 (Chapter 4)
12. Gladysz J.A., Emnet C., and Rábai J. In: Gladysz J.A., Curran D.P., and Horváth I.T. (Eds). Handbook of Fluorous Chemistry (2004), Wiley/VCH, Weinheim 56-100 (Chapter 6)
13. Curran D.P. In: Gladysz J.A., Curran D.P., and Horváth I.T. (Eds). Handbook of Fluorous Chemistry (2004), Wiley/VCH, Weinheim 101-127 (Chapter 7)
14. Curran D.P. In: Gladysz J.A., Curran D.P., and Horváth I.T. (Eds). Handbook of Fluorous Chemistry (2004), Wiley/VCH, Weinheim 128-156 (Chapter 8)
15. Wilcox C.S., Gudipati V., Lu H., Turkyilmaz S., and Curran D.P. Angew. Chem. Int. Ed. 44 (2005) 6938-6940
16. 3COH, see:
17. Knunyants I.L., Dyatkin B.L., and Izv A. Nauk SSSR, Ser. Khim. 5 (1964) 923-925
18. Filler R., and Schure R.M. J. Org. Chem. 32 (1967) 1217-1219
19. Pavlik F.J., and Toren P.E. J. Org. Chem. 35 (1970) 2054-2056
20. Kotun S.P., Anderson J.D.O., and DesMarteau D.D. J. Org. Chem. 57 (1992) 1124-1131
21. Babadzhanova L.A., Kirij N.V., Yagupolskii Yu.L., Tyrra W., and Naumann D. Tetrahedron 61 (2005) 1813-1819
22. F.J. Pavlik, US Patent 3,385,904 (Minnesota Mining and Manufacturing Co.) May 28, 1968 (application: October 30, 1962); Chem. Abstr. 69 (1968) 26753x
23. V. Weinmayr, US Patent 3,317,616 (du Pont de Nemours, E. I., and Co.) May 2, 1967 (application: September 1, 1964); Chem. Abstr. 67 (1967) 63755d
24. A.V. Fokin, I.N. Krotovich, R.Sh. Valiev, Yu. N. Studnev, USSR SU Patent 1,567,566 May 30, 1990 (application: August 15, 1988); Chem. Abstr. 113 (1990) 171491s
25. F.J. Pavlik, US Patent 4,010,212 (Minnesota Mining and Manufacturing Co.) March 1, 1977 (application: June 14, 1976); Chem. Abstr. 86 (1977) 189226
26. Graham D.P., and Weinmayr V. J. Org. Chem. 31 (1966) 957-958
27. Anderson J.D.O., and DesMarteau D.D. J. Fluorine Chem. 77 (1996) 147-152
28. Chen G.J., and Chen L.S. J. Fluorine Chem. 79 (1996) 125-131
29. Rocaboy C., Bauer W., and Gladysz J.A. Eur. J. Org. Chem. 14 (2000) 2621-2628
30. Szlávik Z., Tárkányi G., Gömöry A., Tarczay G., and Rábai J. J. Fluorine Chem. 108 (2001) 7-14
31. Rábai J., Abulikemu A., and Szabó D. In: Gladysz J.A., Horváth I.T., and Curran D.P. (Eds). Handbook of Fluorous Chemistry (2004), Wiley/VCH, Weinheim 421-423 (Chapter 11.27)
32. Abulikemu A., Halász G., Csámpai A., Gömöry A., and Rábai J. J. Fluorine Chem. 125 (2004) 1143-1146
33. Rábai J. In: Gladysz J.A., Horváth I.T., and Curran D.P. (Eds). Handbook of Fluorous Chemistry (2004), Wiley/VCH, Weinheim 156-174 (Chapter 9)
34. Bálint A.-M., Bodor A., Gömöry A., Vékey K., Szabó D., and Rábai J. J. Fluorine Chem. 126 (2005) 1524-1530
35. De Campo F., Lastécouères D., Vincent J.-M., and Verlhac J.-B. J. Org. Chem. 64 (1999) 4969-4971
36. Contel M., Izuel C., Laguna M., Villuendas P.R., Alonso P.J., and Fish R.H. Chem. Eur. J. 9 (2003) 4168-4178
37. Vincent J.-M., Lastécouères D., Contel M., Laguna M., and Fish R.H. In: Gladysz J.A., Horváth I.T., and Curran D.P. (Eds). Handbook of Fluorous Chemistry (2004), Wiley/VCH, Weinheim 298-305 (Chapter 10.12)
38. Vincent J.-M., and Fish R.H. In: Gladysz J.A., Horváth I.T., and Curran D.P. (Eds). Handbook of Fluorous Chemistry (2004), Wiley/VCH, Weinheim 393-394 (Chapter 11.14)
39. Ing H.R., and Manske R.H.F. J. Chem. Soc. (1926) 2348-2351
40. Rábai J., Szabó D., Borbás E.K., Kövesi I., Kövesdi I., Csámpai A., Gömöry A., Pashinnik V.E., and Shermolovich Yu.G. J. Fluorine Chem. 114 (2002) 199-207
41. Szabó D., Bonto A.-M., Kövesdi I., Gömöry A., and Rábai J. J. Fluorine Chem. 126 (2005) 641-652
42. H. Takayanagi, Y. Oohori, Jpn. Kokai Tokkyo Koho JP 10 67,728 (Mitsubishi Chemical Industries Ltd., Japan) March 10, 1998 (application: June 19, 1996); Chem. Abstr. 128 (1998) 257661u.
43. Sebesta D.P., O'Rourke S.S., and Pieken W.A. J. Org. Chem. 61 (1996) 361-362
44. Sebesta D.P., O'Rourke S.S., Martinez R.L., Pieken W.A., and McGee D.P.C. Tetrahedron 52 (1996) 14385-14402
45. Pilichowski J.F., Lehn J.M., Sauvage J.P., and Gramain J.C. Tetrahedron 41 (1985) 1959-1964
46. Alcock N.W., Kingston R.G., Moore P., and Pierpoint C. J. Chem. Soc., Dalton. Trans. (1984) 1937-1943
47. For safety guidelines when working with toxic alkylating reagents including nitrogen mustards see:
48. Wilson E., and Tishler M. J. Am. Chem. Soc. 73 (1951) 3635-3641
49. Kiss L.E., Rábai J., Varga L., and Kövesdi I. Synlett (1998) 1243-1245
50. Szlávik Z., Tárkányi G., Tarczay G., Gömöry A., and Rábai J. J. Fluorine Chem. 98 (1999) 83-87
51. Kiss L.E., Kövesdi I., and Rábai J. J. Fluorine Chem. 108 (2001) 95-109
52. E. de Wolf, Ph.D. Thesis, University of Utrecht, 2002.
53. de Wolf E., Ruelle P., van den Broeke J., Deelman B.-J., and van Koten G. J. Phys. Chem. B 108 (2004) 1458-1466
54. Prevedouros K., Cousins I.T., Buck R.C., and Korzeniowsky S.H. Environ. Sci. Technol. 40 (2006) 32-44
55. Wallington T.J., Hurley M.D., Xia J., Wuebbles D.J., Sillman S., Ito A., Penner J.E., Ellis D.A., Martin J., Mabury S.A., Nielsen O.J., and Sulbaek Andersen M.P. Environ. Sci. Technol. 40 (2006) 924-930
56. Sargent R.S., Meshri D.T., Grigat M., and Dattatray U. Proceedings of the INTERSIBFLUORINE-2006. Tomsk, Russia, June (2006). 5-901-688-09-0 253-255
57. Dear R.E.A., Fox W.B., Fredericks R.J., Gilbert E.E., and Huggins D.K. Inorg. Chem. 9 (1970) 2590-2591