알킬나프탈렌이 치환된 페로센 중합체의 단계적 합성

장길수; Killsoo Jang

Polymer(Korea), Vol.23, No.6, 781-790, November, 1999

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알킬나프탈렌이 치환된 페로센 중합체의 단계적 합성

Stepwise Preparation of Alkylnaphthalene-Substituted Ferrocene Polymers

장길수 ^†

금호석유화학(주)

Killsoo Jang^†

Korea Kumho Petrochemical Co., Ltd., 680 Sangkae-Dong, Nam-ku, Ulsan 680-180, Korea

E-mail:

초록

면과 면을 마주하는 페로센-페로센 고분자의 중합방법에 대하여 알아본다. 이 방법은 4-(n-decyl)-1,8-diiodonaphthalene을 cyclopentadienyl copper dimethyl sulfide와 -25 ℃에서 짝

A new synthetic route to face-to-face ferrocene polymers is studied. This route involves stepwise construction of a monomer unit by coupling cyclopentadienyl copper dimethyl sulfide at -25 ℃ with 4-(n-decyl)-1,8-diiodonaphthalene. The resulting mixture of 1-cyclopentadienyl-4- and 1-cyclopentadienyl-5-(n-decyl)-8-iodonaphthalene is then converted to the corresponding ferrocene by successive treatment with base and ferrous chloride. Finally, the remaining iodosubstituents are replaced by cyclopentadienyl groups by treatment with CpCuSMe₂. Polymerization of the monomer is carried out by continuous treatment with base and ferrous chloride. The polymer with 17 ferrocene units is obtained. This stepwise synthetic route is milder than the previous palladium-catalyzed and can be used for the synthesis of the higher molecular weight polymers.

Keywords:ferrocene polymer;stepwise construction;face-to-face

[References]

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Jang K, Polym.(Korea), 22(6), 890 (1998)
Nugent HM, Rosenblum M, Klemarczyk P, J. Am. Chem. Soc., 115, 3848 (1993)
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Kasahara A, Izumi T, Yoshida Y, Shimizu I, Bull. Chem. Soc. Jpn., 55, 1901 (1982)
Gronbeck DA, Ph.D. Dissertation, Brandeis Univ. (1991)
Nilsson M, Wahren R, Wennerstrom O, Tetrahedron Lett., 4583 (1970)
Wilcox CF, Carparter BK, J. Am. Chem. Soc., 101, 3897 (1979)
Wahren R, Organomet. Chem., 57, 415 (1973)
Wannagat U, Niederprun H, Ber., 94, 1540 (1961)
Gilman H, Brannen CG, Ingham RK, J. Org. Chem., 22, 685 (1957)
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Rylander PN, "Catalytic Hydrogenation over Platinum Metals," Academic Press, New York (1967)

[1] Arnold R, Matchett SA, Rosenblum M, Organometallics, 7, 2261 (1988)

[2] Jang K, Polym.(Korea), 22(6), 890 (1998)

[3] Nugent HM, Rosenblum M, Klemarczyk P, J. Am. Chem. Soc., 115, 3848 (1993)

[4] Rosenblum M, Nugent HM, Jang KS, Labes MM, Cahalane W, Klemarczyk P, Reiff WM, Macromolecules, 28(18), 6330 (1995)

[5] Gronbeck DA, Matchett SA, Rosenblum M, Tetrahedron Lett., 30, 2811 (1989)

[6] Kasahara A, Izumi T, Yoshida Y, Shimizu I, Bull. Chem. Soc. Jpn., 55, 1901 (1982)

[7] Gronbeck DA, Ph.D. Dissertation, Brandeis Univ. (1991)

[8] Nilsson M, Wahren R, Wennerstrom O, Tetrahedron Lett., 4583 (1970)

[9] Wilcox CF, Carparter BK, J. Am. Chem. Soc., 101, 3897 (1979)

[10] Wahren R, Organomet. Chem., 57, 415 (1973)

[11] Wannagat U, Niederprun H, Ber., 94, 1540 (1961)

[12] Gilman H, Brannen CG, Ingham RK, J. Org. Chem., 22, 685 (1957)

[13] Sergievskaya SI, Safonova TS, J. Gen. Chem. USSR, 27, 477 (1957)

[14] Rylander PN, "Catalytic Hydrogenation over Platinum Metals," Academic Press, New York (1967)