Regioselective azidolysis of epoxides in water using poly(vinylamine) and poly(allylamine) as new polymeric cosolvents

Iranian Polymer Journal (English Edition)

Volumn 13, Issue 1, 2004, Pages 21-28

  Tamami, Bahman ^a   Kolahdoozan, Majid ^a   Mahdavi, Hossein ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

Azidohydrine; Epoxide; Poly(allylamine); Poly(vinylamine); Polymeric cosolvent

Indexed keywords

CATALYSTS; ORGANIC SOLVENTS; SOLUBILITY; SYNTHESIS (CHEMICAL); THERMAL EFFECTS; WATER;

AZIDOLYSIS; EPOXIDES; POLYALLYLAMINE; POLYMERIC COSOLVENTS; POLYVINYLAMINE;

ORGANIC POLYMERS;

EID: 1542604374     PISSN: 10261265     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (44)

1. Lindestrom U.M., Stereoselective organic reactions in water, Chem. Rev., 102, 2751-2772 (2002).
2. Yalkowsky S.H., Solubility and Solubilization in Aqueous Media, Oxford University, New York (1999).
3. Regen S.L., Nigam A., and Besse J., Triphase catalysis. Insoluble hexamethylphosphoramide as a solid solvent, Tetrahedron Lett., 19, 2757-2760 (1978).
4. Tomoi M., Ikeda M., and Kakiuchi H., Polymer-supported phosphoric triamides as catalysis for phase-transfer reactions, Tetrahedron Lett., 19, 3757-3758 (1978).
5. Regen S.L., Mehrota A., and Singh A., Poly(acrylamide)-based solid-phase cosolvents, J. Org. Chem., 46, 2182-2184 (1981).
6. Kondo S., Ohta K., and Tsuda K., Polymeric sulfoxides: Effective catalysts in two phase reactions, Makromol. Chem., Rapid Commun., 4, 145-148 (1983).
7. Kondo S., Inagaki Y., and Tsuda K., Syntheis of polymeric formamides and their use as phase transfer catalysis. J. Polym. Sci., Polym. Lett. Ed., 22, 249-254 (1984).
8. Kondo S., Yasui H., Ohta K., and Tsuda K., Polymeric sulphones as phase transfer catalysts, J. Chem. Soc., Chem. Commun., 400-401 (1985)
9. Kelly J., MacKenzie W.M., and Sherrington D.C., Linear polymers and block copolymers as solid-liquid phase transfer catalysts, Polymer, 20, 1048-1050 (1979).
10. Regon S.L., and Dulak L., Solid phase cosolvents, J. Am. Chem. Soc., 99, 623-625 (1977).
11. McKenzie W.M., Sherrington D.C., Polymer-supported phase transfer catalysis in solid-liquid reactions, J. Chem. Soc., Chem. Commun., 541-543 (1978).
12. Patai S., Ed., The Chemistry of Azido Group, Wiley, New York, (1971).
13. Tanmaya P., Azidonucleosides: Synthesis, reactions and biological properties, Chem. Rev., 102, 1623-1667 (2002).
14. Seriven E.F.V. and Turnbull K., Azides: Their preparation and synthetic methods, Chem. Rev., 88, 297-368 (1988).
15. Coe D.M., Myer P.L., Parry D.M., Roberts S.M., and Storer R., Synthesis of compounds active against HIV. Part 2. Preparation of some 2′,3′-dideoxy-6′-florocarboxylic nucleosides, J. Chem. Soc., Chem. Commun., 151-153 (1990).
16. Jacobs G.A., Tino J.A., and Zahler R., Synthesis of SQ-32,829, a new nucleoside antiviral agent, Tetrahedron Lett., 30, 6955-6958 (1989).
17. Smith B.T., Gracias V., and Anube J., Regiochemical studies of ring expansion of hydroxy azides with cyclic ketones, J. Org. Chem., 65, 3771-3774 (2000).
18. Badiang J.G. and Aube J., One-step conversion of aldehydes to oxazolines and 5,6-dihydro-4H-1,3-oxazines using 1,2- and 1,3-azido alcohols, J. Org. Chem., 61, 2484-2487 (1996).
19. Fringuelli F., Piermatti O., Pizzo F., and Vaccaro L., Ring opening of epoxides with sodium azide in water. A regioselective pH-controlled reaction, J. Org. Chem., 64, 6094-6096 (1999).
20. VanderWerf C.A., Heisler R.Y., and McEwen W.E., The reaction of sodium azide with some representative epoxides, J. Am. Chem. Soc., 76, 1231-1235 (1954).
21. Lorenzin M., Guerriero A., and Pietra F., Reaction of primary -azido tertiary alcohols with nitrosonium salts. A rearrangement related to the Tiffeneau reaction, J. Org. Chem., 45, 1704-1705 (1980).
22. Chini M., Crotti P., and Macchia F., Efficient metal salt catalyzed azidolysis of epoxides with azide in acetonitrile, Tetrahedron Lett., 31, 5641-5644 (1990).
23. Meguro M., Asao N., and Yamamoto Y., Ytterbium tri-isopropoxide catalysed ring opening of epoxides with trimethylsilyl azide, J. Chem. Soc., Chem. Commun., 1021-1022 (1995).
24. Caron M., and Sharrpless K.B., Ti(O-i-Pr)4-mediated nucleophilic opening of 2,3-epoxyalcohols. A mild procedure for regioselective ring-opening, J. Org. Chem., 50, 1557-1560 (1985).
25. 4, Tetrahedron Lett., 27, 4423-4426 (1986).
26. Blandy C., Choukroun R., and Gervais D., Synthesis of o-protected azidohydrines catalysed by titanium and vanadium complexes, Tetrahedron Lett., 24, 4189-4192 (1983).
27. Leung W.H., Wu M.C., Chim J.L.C., Yu M.T., Hou H.W., Yeung L.L., Wong W.T., and Wang Y., Epoxides ring opening catalysed by imidochromium complexes, J. Chem. Soc., Dalton Trans., 3525-3529 (1997).
28. Saito S., Yamashitac S., Nishikawa T., Yokoyama Y., Inaba M., and Moriwake T., Highly nucleophilic tributyltin azide in oxirane ring cleavage leading to 1,2-azido alcohol, Tetrahedron Lett., 30, 4153-4156 (1989).
29. 2]: Synthesis of -amino acids, J. Org. Chem., 53, 5185-5187 (1988).
30. Youn Y.S., Cho I.S., and Chung B.Y., Lithium azidohydridodiisobutylaluminate in THF as an efficient azide donor, Tetrahedron Lett., 39, 4337-4338 (1998).
31. Saito S., Nishikawa T., Yokoyama Y., and Moriwake T., Efficient nucleophilic oxirane ring cleavage with dibutyltin diazide, Tetrahedron Lett., 31, 221-224 (1990).
32. Mereyala H.B. and Frei B., Preparation of vicinal azidohydrines by reactions of oxiranes with triethylaluminium/hydrogen azide, Helv. Chem. Acta, 69, 415-418 (1986).
33. Benedetti F., Berti F., and Norbedo S., Regio- and stereoselective ring opening of 2,3-epoxyalcohols with diethylaluminium azide, Tetrahedron Lett., 39, 7971-7974 (1998).
34. Weghe P.V.D. and Collin J., Ring opening reactions of epoxides catalysed by samarium iodides, Tetrahedron Lett., 36, 1649-1652 (1995).
35. 3 as an efficient Lewis acid catalyst in water, Tetrahedron Lett., 42, 1131-1133 (2001).
36. Schneider C., Quaternary ammonium salt catalyzed azidolysis of epoxides with trimethylsilyl azide, Synlett, 12, 1840-1842 (2000).
37. 3-anion, J. Org. Chem., 55, 4892-4897 (1990).
38. Tamami B. and Mahdavi H. Synthesis of azidohydrins from epoxides using quaternized amino functionalized cross-linked polyacrylamide as a new polymeric phase-transfer catalyst, Tetrahedron Lett., 42, 8721-8724 (2001).
39. Onaka M., Sugita K., and Izumi Y., Solid-supported sodium azide reagents: Their application and reactions with epoxides, J. Org. Chem., 54, 1116-1123 (1989).
40. Tamami B. and Mahdavi H., Synthesis of halohydrines from epoxides using quaternized amino functionalized cross-linked polyacrylamide as a new solid-liquid phase-transfer catalyst, React. Funct. Polym., 51, 7-13 (2002).
41. Tamami B. and Mahdavi H., Synthesis of thiocyanohydrines from epoxides using quaternized amino functionalized cross-linked polyacrylamide as a new solid-liquid phase-transfer, catalyst, Tetrahedron Lett., 43, 6225-6228 (2002).
42. Wang H., Ma J., Zhang Y., and He B., Adsorption of bilirubin on the polymeric β-cyclodextrin supported by partially aminated polyacrylamide gel, React. Funct. Polym., 32, 1-7 (1997).
43. Tomoi M. and Ford W.T., Mechanisms of polymer-supported catalysis. 1. Reaction of 1-bromooctane with aqueous sodium cyanide catalyzed by polystyrene-bound benzyltri-n-butylphosphinium ion, J. Am. Chem. Soc., 103, 3821-3838 (1981).
44. Sutowardoyo K.I., Emaziane M., Lhoste P., and Sinou D., Highly regio and chemoselective ring opening of epoxides with trimethylsilyl azide in the presence of aluminium isopropoxide azide titanium isopropoxide, Tetrahedron, 47, 1435-1446 (1991).