Cation and leaving group effects in isosorbide alkylation under microwave in phase transfer catalysis

Tetrahedron

Volumn 57, Issue 20, 2001, Pages 4365-4370

  Chatti, Saber ^a   Bortolussi, Michel ^a   Loupy, André ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

Alkylation; Cation and leaving group; Microwave; Phase transfer catalysis

Indexed keywords

BROMIDE; CATION; ISOSORBIDE; MESYLIC ACID; SODIUM CHLORIDE; SOLVENT; TOLUENESULFONIC ACID DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPARATIVE STUDY; HEATING; MICROWAVE IRRADIATION; PHASE TRANSITION; PRIORITY JOURNAL; REACTION ANALYSIS; STOICHIOMETRY; TEMPERATURE;

EID: 0035858666     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)00318-0     Document Type: Article

References (42)

1. Flèche G., Huchette M. Starch/Stärke. 38:1986;26.
2. Jacquet F., Gaset A., Gorrichon J.P. Inform. Chim. 30:1984;1431.
3. Kricheldorf H.R. Rev. Macromol. Chem. Phys. 37:1997;599.
4. Stross P., Hemmer R. Adv. Carbohydr. Chem. Biochem. 49:1991;93.
5. Chatti S., Bortolussi M., Loupy A. Tetrahedron Lett. 41:2000;3367.
6. Chatti S., Bortolussi M., Loupy A. Tetrahedron. 56:2000;5877.
7. Majdoub M., Loupy A., Flèche G. Eur. Polym. J. 30:1994;1431.
8. Thiem J., Lüders H. Polym. Bull. (Berlin). 11:1984;365.
9. Thiem J., Lüders H. Starch/Stärke. 36:1984;170.
10. Storbeck R., Rehahn M., Ballauff M. Makromol. Chem. 194:1994;53.
11. Cognet-Georjon E., Méchin F., Pascaut J.P. Makromol. Chem. Phys. 196:1995;3733.
12. Bachmann F., Reimer J., Ruppenstein M., Thiem. J. Macromol. Rapid Commun. 19:1998;21.
13. Meng Q., Thibblin A. J. Am. Chem. Soc. 117:1995;9399.
14. Bartsch R.A., Bunnett J.F. J. Am. Chem. Soc. 91:1969;1376.
15. Veeravagu P., Arnold R.T., Eigenmann G.W. J. Am. Chem. Soc. 86:1964;3072.
16. Shaffer T.D., Antolin K., Percec V. Makromol.Chem. 188:1987;1033.
17. Chang C., Kiesel R.F., Hogen-Esch T. J. Am. Chem. Soc. 95:1973;8446.
18. Pocker Y., Ronald B.P. J. Am. Chem. Soc. 100:1978;2795.
19. Epiotis N.D., Cherry W.R., Shaik S., Yates R., Bernardi F. Topics Current Chem. 1977;70.
20. Bunnett J.F., Zahler R.E. Chem. Rev. 49:1951;273.
21. Talma A.G., Vossen H., Sudhölter E.J.R., Eerden J., Reinhoudt D.N. Synthesis. 1985;2241.
22. Reinhoudt D.N., Jong F., Tomassen H.P.M. Tetrahedron Lett. 22:1979;2067.
23. Danilova O.I., Esikova I.A., Yufit S.S. Izv. Akad. Nauk SSSR Ser. Khim. 1986;2422.
24. Yufit S.S., Zinovyev S.S. Tetrahedron. 55:1999;6319.
25. Loupy A., Pardo C. Synthetic Commun. 18:1988;1275.
26. Cohen S., Zoran A., Sasson Y. Tetrahedron Lett. 39:1998;9815.
27. Starks C.M. J. Am. Chem. Soc. 93:1971;195.
28. Pauling L. The Chemical Bond. 1967;Cornell University Press, London.
29. Handbook of Chemistry and Physics. 57th :1976;:1977;F109 CRC Press, Boca Raton, FL.
30. Hajek, M., Radoiu, M. Second World Congress on Microwave and Radio Frequency Processing, Orlando (USA), April 2-6, 2000. Comm. MWB-CP2-02.
31. Vidal T., Petit A., Loupy A., Gedye R.N. Tetrahedron. 56:2000;5473.
32. Bogdal D., Pielichowski J., Boron A. Synlett. 1996;873.
33. Jinchang D., Hangjie G., Jinzhu W., Caizhen L. Synthetic Commun. 24:1994;301.
34. Rechsteiner B., Texier-Boullet F., Hamelin J. Tetrahedron Lett. 32:1993;5074.
35. Varma R.S., Dahiya R., Kumar S. Tetrahedron Lett. 38:1997;2039.
36. Lewis D.A., Summers J.D., Ward T.C., McGrath J.C. J. Polym. Sci. 30A:1992;1647.
37. Bougrin K., Kella Bennani A., Fkih-Tétouani S., Soufiaoui M. Tetrahedron Lett. 35:1994;8373.
38. Gedye R.N., Westaway K.C. J. Microwave Power and Electromag Energy. 1995;219.
39. Deshayes S., Liagre M., Loupy A., Luche J.L., Petit A. Tetrahedron. 55:1999;1085. (Tetrahedron Report No. 501).
40. Yoshida Y., Shimonishi K., Sakakura Y., Okada S., Aso N., Tanabe Y. Synthesis. 9:1999;1663.
41. Burns D.H., Miller J.D., Chan H.K., Delaney M.O. J. Am. Chem. Soc. 119:1997;2125.
42. Harada T., Kaneko F., Oku A. Tetrahedron. 54:1998;9317.