포스파젠 고분자를 이용한 Wittig반응에 관한 연구

권석기; 전창림

Journal of the Korean Industrial and Engineering Chemistry, Vol.5, No.5, 843-850, October, 1994

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포스파젠 고분자를 이용한 Wittig반응에 관한 연구

Studies on Polyphosphazenes-bound Wittig Reactions

권석기, 전창림

초록

[NP(OC₆H₅)_1.7(OC₆H₄P(Ph)₂=CHCH₂CH₂CH₃)_0.3]_n과 같은 포스파젠 고분자에 부착된 Wittig 시약을 [NP(OC₆H₅)_1.7(OC₆H₄Br)_0.3]_n에 n-butyllithium, diphenylchlorophosphine, 그리고 n-butyl iodide 등으로 처리하여 만들었다. 고분자의 반응들은 [N₃P₃(OC₆H₅)₅(OC₆H₄P(Ph)₂)]와 같은 고리형 삼중체를 이용한 모델반응 조건들을 고려해 이루어졌다. 포스파젠 고분자에 부착된 Wittig 시약과 benzophenone을 반응시켜 원하는 알켄과 고분자에 부착된 phosphine oxide를 성공적으로 만들었다.

Polyphosphazene-bound Wittig reagents such as [NP(OC₆H₅)_1.7(OC₆H₄P(Ph)₂=CHCH₂CH₂CH₃)_0.3]_n were synthesized by treating [NP(OC₆H₅)_1.7(OC₆H₄Br)_0.3]_n with n-butyllithium, diphenylchlorophosphine, and n-butyl iodide. Polymeric reactions were carried out according to the reaction conditions with cyclic primers such as [N₃P₃(OC₆H₅)₅(OC₆H₄P(Ph)₂)]. The desired alkene and polymer-bound phosphine oxide were prepared successfully by the reaction of polyphosphazene-bound Wittig reagents with benzophenone.

[References]

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[1] Hodge P, Sherrington DC, "Polymer-Supported Reactions in Organic Synthesis," Wiley, London (1980)

[2] Akelah A, Sherrington DC, Chem. Rev., 81, 557 (1982)

[3] Roman E, Valenzuela G, J. Polym. Sci., 21, 2057 (1983)

[4] Frechet J, Schnerch C, J. Am. Chem. Soc., 93, 492 (1971)

[5] Frechet J, Tetrahedron, 37, 663 (1981)

[6] Camps F, Castells J, Fout J, Tetrahedron Lett., 1715 (1971)

[7] Bernard M, Ford WT, J. Org. Chem., 48, 326 (1983)

[8] Castells J, Font J, J. Chem. Soc.-Perkin Trans. 1, 1, 1 (1979)

[9] Akelah A, Eur. Polym. J., 18, 559 (1982)

[10] Clarke S, Harrison CR, Hodge P, Tetrahedron Lett., 21, 1375 (1980)

[11] Hodge P, Waterhouse J, Polymer, 22, 1153 (1981)

[12] Heitz W, Michels R, Justus Liebigs Ann. Chem., 227 (1973)

[13] Heitz W, Michels R, Angew. Chem.-Int. Edit., 11, 298 (1972)

[14] Allcock HR, Chem. Rev., 72, 315 (1972)

[15] Allcock HR, Fuller TJ, Macromolecules, 13, 1338 (1980)

[16] Allcock HR, Kwon S, Macromolecules, 19, 1502 (1986)

[17] Allcock HR, Chem. Eng. News, 63, 22 (1985)

[18] Allcock HR, Kwon S, Macromolecules, 22, 75 (1989)

[19] Allcock HR, Kwon S, Riding RJ, Biomaterials, 9, 509 (1988)

[20] Allcock HR, Gebura M, Kwon S, Biomaterials, 9, 500 (1988)

[21] Allcock HR, Kwon S, Macromolecules, 21, 1980 (1988)

[22] Allcock HR, "Phosphorous-Nitrogen Compounds," Academic Press, New York (1972)

[23] Allcock HR, Fuller JR, Evans TL, Macromolecules, 13(6), 1326 (1980)

[24] Austin PE, Riding GH, Allcock HR, Macromolecules, 16, 719 (1983)