고분자 물질로 지지된 크라운 에테르류: 5. Lariat Azacrown Ether의 합성

심재우; 정광보; 友井正男

Polymer(Korea), Vol.16, No.3, 285-290, May, 1992

Polymer-Supported Crown Ethers: 5. Synthesis of Lariat Azacrown Ethers

Immobilization methods of lariat azacrown ether, containing oxyethylene spacer in the sidearm of crown ring, on the polymer matrix were studied. Crown ethers bound to polystyrene resins by oxyethylene spacer were obtained by the reaction of monoazacrown ether with 2-tosyloxyethoxy- or 2-(2-tosyloxyethoxy)ethoxy methylated polystyrene resins, derived from tosylation of 2-hydroxyethoxy- or 2-(2-hydroxyethoxy)ethoxymethylated polystyrene resins. This method presented a convenient route to immobilize various crown ether structure on polystyrene supports by poly(oxyethylene) spacers. Polymer supported simple crown ethers without oxygen donors in the spacer chain corresponding to the above lariat azacrowns were obtained by the reaction of crosslinked ω-bromoalkylated polystyrene resins with monoazacrown ether.

[References]

Regen SL, Angew. Chem.-Int. Edit., 18, 421 (1979)
Montanari F, Landini D, Rolla F, Topics in Current Chemistry, 101, 147 (1982)
Ford WT, Tomoi M, Adv. Polym. Sci., 55, 49 (1984)
Smid J, Sinta R, Topics in Current Chemistry, 121, 105 (1984)
Tomoi M, Ford WT, Syntheses and Separations Using Functional Polymer, D.C. Sherrington and P. Hodge, Eds., Wiley, Chichester (1988)
vanZon A, deJong F, Onwezen Y, Recl. Trav. Chim. Pays-Bas, 100, 429 (1981)
Manecke G, Kramer A, Makromol. Chem., 182, 3017 (1981)
Tomoi M, Yanai N, Shiiki S, Kakiuchi H, J. Polym. Sci. A: Polym. Chem., 22, 911 (1984)
Anelli PL, Czech B, Montanari F, Quici S, J. Am. Chem. Soc., 106, 861 (1984)
Montanari F, Quici S, Anelli PL, Br. Polym. J., 16, 212 (1984)
Pugia MJ, Czech A, Czech BP, Bartsch RA, J. Org. Chem., 51, 2945 (1986)
Gokel GW, Korzeniowski SH, Macrocyclic Polyether Syntheses, Springer-Verlag, Berlin (1982)
Gokel GW, "New Chemistry, Catalysis, and Application," in "Phase-Transfer Catalysis," C.M. Starks, ed., ACS Symp. Ser., 326, Am. Chem. Soc., Washington, D.C. (1987)
Weber E, "Crown Ether and Analogs," S. Patai, Z. Rappoport, eds., Wiley, New York (1984)
Gokel GW, Trafton JE, "Cation Binding by Macrocycles," Y. Inoue, G.W. Gokel, Eds., Marcel Dekker, New York (1990)
Bull. Korean Chem. Soc., to Submitted
Tomoi M, Ford WT, J. Am. Chem. Soc., 103, 3821 (1981)
Tomoi M, Oda H, Kakiuchi H, Makromol. Chem., 189, 277 (1985)
Darling GD, Frechet JMJ, J. Org. Chem., 51, 2270 (1986)
Valter B, Janout V, Hrudkova H, Cefelin P, Lukyanenko NG, Basok SS, Kurigina EY, Polym. Bull., 22, 261 (1989)
Tomoi M, Ogawa E, Hosokawa Y, Kakiuchi H, J. Polym. Sci. A: Polym. Chem., 20, 3421 (1982)
Tomoi M, Suzuki T, Kakiuchi H, React. Polym., 10, 27 (1989)

[Referenced By]

[1] Regen SL, Angew. Chem.-Int. Edit., 18, 421 (1979)

[2] Montanari F, Landini D, Rolla F, Topics in Current Chemistry, 101, 147 (1982)

[3] Ford WT, Tomoi M, Adv. Polym. Sci., 55, 49 (1984)

[4] Smid J, Sinta R, Topics in Current Chemistry, 121, 105 (1984)

[5] Tomoi M, Ford WT, Syntheses and Separations Using Functional Polymer, D.C. Sherrington and P. Hodge, Eds., Wiley, Chichester (1988)

[6] vanZon A, deJong F, Onwezen Y, Recl. Trav. Chim. Pays-Bas, 100, 429 (1981)

[7] Manecke G, Kramer A, Makromol. Chem., 182, 3017 (1981)

[8] Tomoi M, Yanai N, Shiiki S, Kakiuchi H, J. Polym. Sci. A: Polym. Chem., 22, 911 (1984)

[9] Anelli PL, Czech B, Montanari F, Quici S, J. Am. Chem. Soc., 106, 861 (1984)

[10] Montanari F, Quici S, Anelli PL, Br. Polym. J., 16, 212 (1984)

[11] Pugia MJ, Czech A, Czech BP, Bartsch RA, J. Org. Chem., 51, 2945 (1986)

[12] Gokel GW, Korzeniowski SH, Macrocyclic Polyether Syntheses, Springer-Verlag, Berlin (1982)

[13] Gokel GW, "New Chemistry, Catalysis, and Application," in "Phase-Transfer Catalysis," C.M. Starks, ed., ACS Symp. Ser., 326, Am. Chem. Soc., Washington, D.C. (1987)

[14] Weber E, "Crown Ether and Analogs," S. Patai, Z. Rappoport, eds., Wiley, New York (1984)

[15] Gokel GW, Trafton JE, "Cation Binding by Macrocycles," Y. Inoue, G.W. Gokel, Eds., Marcel Dekker, New York (1990)

[16] Bull. Korean Chem. Soc., to Submitted

[17] Tomoi M, Ford WT, J. Am. Chem. Soc., 103, 3821 (1981)

[18] Tomoi M, Oda H, Kakiuchi H, Makromol. Chem., 189, 277 (1985)

[19] Darling GD, Frechet JMJ, J. Org. Chem., 51, 2270 (1986)

[20] Valter B, Janout V, Hrudkova H, Cefelin P, Lukyanenko NG, Basok SS, Kurigina EY, Polym. Bull., 22, 261 (1989)

[21] Tomoi M, Ogawa E, Hosokawa Y, Kakiuchi H, J. Polym. Sci. A: Polym. Chem., 20, 3421 (1982)

[22] Tomoi M, Suzuki T, Kakiuchi H, React. Polym., 10, 27 (1989)