Synthesis of 1,1,1-Triethoxycarbonyl-3-[2-(F-alkyl)-ethyl]propanes and 1,1,q,q-Tetraalkoxycarbonyl-1,q-di-[2-(F-alkyl)-ethyl]alcanes as Precursors of Anionic Surfactants

References

1. Jouani, M. A., Szönyi, S., Trabelsi, H., Dieng, S. Y., Watzke, H. J. and Cambon, A.: Synthesis and aggregation properties of new fluorine-containing double-chain amphiphiles derived from di- and tri-substituted ureas, Supramol. Sci.2, 117–123 (1995). 10.1016/0968-5677(96)89076-6Search in Google Scholar

2. Dieng, S. Y., Szönyi, S., Jouani, M. A., Watzke, H. J. and Cambon, A.: Synthesis and physiochemical properties of new vesicle-forming fluorosurfactants derived from substituted di-thioacetamides, Colloids Surf., A 98 (1/2), 43–51 (1995).Search in Google Scholar

3. Jouani, M. A., Szönyi, S., Wehrli, E. and Cambon, A.: Synthesis and liposome formation of new synthetic perfluoralkylated cationic lipids derived from N-[[2-(F-alkyl)-ethylthio]methyl (or propyl)] N′-(2-dimethylaminoethyl)ureas, J. Liposome Res.9, 95–114 (1999). 10.3109/08982109909044494Search in Google Scholar

4. Trabelsi, H., Szönyi, S., Reuter, P., Wehrli, E. and Geribaldi, S.: Synthesis and vesicle formation of ethyl 2-[2′-(F-alkyl)-ethyl]2-alkyl malonic acid disodium salts, Supramol. Chem.13, 583–591 (2001). 10.1080/10610270108039791Search in Google Scholar

5. Edwards, C. M., Lowe, K. C., Trabelsi, H., Lucas, P. and Cambon, A.: Novel fluorinated surfactants for perfluorochemical emulsification: biocompatibility assessments of glycosidic and polyol derivatives, Art. Cells, Blood Subs., Immob. Biotechnol.25, 327–333 (1996). 10.3109/10731199709118922Search in Google Scholar

6. Guittard, F., Taffin de Givenchy, E., Geribaldi, S. and Cambon, A.: Highly fluorinated thermotropic liquid crystals: an update, J. Fluorine Chem.100, 85–96 (1999). 10.1016/S0022-1139(99)00205-5Search in Google Scholar

7. Trabelsi, H., Szönyi, F. and Geribaldi, S.: Nucleophilic displacements of 2-perfluoroalkyl-1-iodoethanes: improved synthesis of fluorine-containing malonic esters, J. Fluorine Chem.107, 177–181 (2001). 10.1016/S0022-1139(00)00388-2Search in Google Scholar

8. Trabelsi, H. and Cambon, A.: FR Demande Nr. 2, 765, 217 (1998).Search in Google Scholar

9. Szönyi, F. and Cambon, A.: Addition of dichlorocarbene on organic azides in solid-liquid phase-transfer catalysis, Tetrahedron Lett.33, 2339–2342 (1992). 10.1016/S0040-4039(00)74205-5Search in Google Scholar

10. Bollens, E., Szönyi, F. and Cambon, A.: Synthese des isothiocyanates de 2-F-alkyl ethyle à longue chaîne, J. Fluorine Chem.53, 1–14 (1991). 10.1016/S0022-1139(00)82234-4Search in Google Scholar

11. Jouani, A. M., Szönyi, F. and Cambon, A.: Synthese des isocyanates de 2-F-alkylethyle, J. Fluorine Chem.56, 85–92 (1992). 10.1016/S0022-1139(00)80183-9Search in Google Scholar

12. Trabelsi, H., Szönyi, F., Michelangeli, N. and Cambon, A.: Synthese des 2-F-alkyléthylamines: optimisation de l'obtention des azotures de 2-F-alkyléthyle et de leur réduction en amines, J. Fluorine Chem.69, 115–117 (1994). 10.1016/0022-1139(94)03066-9Search in Google Scholar

13. Guennouni, F., Szönyi, F. and Cambon, A.: New and effective route to N-methyl 2-F-alkylethylamines, Synth. Commun.24, 2653–2660 (1994). 10.1080/00397919408010578Search in Google Scholar

14. Brace, N. O.: Reactions of 1-iodo-2-perfluorocyclohexane conformers-products of elimination and reduction-rates and mechanisms, J. Am. Chem. Soc.88, 2428–2434 (1964). 10.1021/ja01066a027Search in Google Scholar

15. Brace, N. O., Marshall, L. W., Pinson, C. J. and Van Windergen, G.: Effect of a perfluoroalkyl group on the elimination and substitution reactions of two homologous series of perfluoroalkyl-substituted iodoalkanes., J. Org. Chem49, 2361–2368 (1984). 10.1021/jo00187a012Search in Google Scholar

16. Szönyi, F. and Cambon, A.: Fonctionnalisation des iodures de F-alkyl-2 ethane par catalyse par transfert de phase: importance de cette technique en série F-alkylée, J. Fluorine Chem.42, 59–68 (1989). 10.1016/S0022-1139(00)83967-6Search in Google Scholar

17. Lukyanenko, N.: Crownethers: application to organic synthesis (part 1), Janssen Chim. Acta9, 3–10 (1991).Search in Google Scholar

18. Lukyanenko, N.: Crownethers: Application to organic synthesis (part 2), Janssen Chim. Acta10, 12–18 (1992).Search in Google Scholar

19. Pedersen, C. J.: Cyclic polyethers and their complexes with metal salts, J. Am. Chem. Soc.89, 2495–2496 (1967). 10.1021/ja00986a052Search in Google Scholar

20. Fedorynski, M. F., Wojciechowski, W., Matacz, Z. and Makosza, M.: Sodium and potassium carbonates: efficient strong bases in solid liquid two-phases systems, J. Org. Chem.43, 4682–4684 (1978). 10.1021/jo00418a043Search in Google Scholar