Optically active polymer synthesis by Diels-Alder polymerization with chirally modified Lewis acid catalyst

被引：57

作者：

Kamahori, K ^{[1
]}

Tada, S ^{[1
]}

Ito, K ^{[1
]}

Itsuno, S ^{[1
]}

机构：

[1] Toyohashi Univ Technol, Dept Mat Sci, Toyohashi, Aichi 4418580, Japan

来源：

MACROMOLECULES | 1999年 / 32卷 / 03期

关键词：

D O I：

10.1021/ma9815410

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

A series of copolymers have been synthesized by Diels-Alder polymerization of bisdienophile monomer with bisdiene monomer. Bismaleimides (1) and bis(alpha,beta-unsaturated ester)s (4) were prepared and used as bisdienophile monomer. Furfuryl and butadienyl moieties were chosen as the diene part of the bisdiene monomers (2, 5). Repetitive Diels-Alder reactions between these monomers in the presence of Lewis acid catalyst yielded alternative Diels-Alder polymers (6, 12, 18, 15). On the basis of these results, asymmetric Diels-Alder polymerization was investigated. The use of enantiopure Lewis acid catalysts (7-10) in the Diels-Alder polymerization of above monomers resulted in the formation of optically active polymers having the asymmetric carbons in their main chain.

引用

页码：541 / 547

页数：7

共 40 条

[1] SYNTHESIS OF NEW POLYIMIDES BY DIELS-ALDER REACTION OF BIS(2-PYRONE)S WITH BISMALEIMIDES [J].

ALHAKIMI, G ;

KLEMM, E ;

GORLS, H .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 1995, 33 (07) :1133-1142

[2] SULFUR-CONTAINING OPTICALLY-ACTIVE POLYMERS .3. SYNTHESIS AND CHIROPTICAL PROPERTIES OF OPTICALLY-ACTIVE POLY(GAMMA-KETOSULFIDE)S PREPARED BY POLYADDITION OF 1,3-DIMERCAPTOBENZENE TO TRANS,TRANS-DIBENZYLIDENE ACETONE IN THE PRESENCE OF CHIRAL AMINES [J].

ANGIOLINI, L ;

CARETTI, D ;

CARLINI, C ;

SALATELLI, E .

POLYMER, 1995, 36 (05) :1071-1082

[3] VAULTED BIARYLS AS CHIRAL LIGANDS FOR ASYMMETRIC CATALYTIC DIELS-ALDER REACTIONS [J].

BAO, JM ;

WULFF, WD ;

RHEINGOLD, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (09) :3814-3815

[4] POLYMERS WITH MAIN-CHAIN CHIRALITY - SYNTHESIS OF HIGHLY ISOTACTIC, OPTICALLY-ACTIVE POLY(4-TERT-BUTYLSTYRENE-ALT-CO) USING PD(II) CATALYSTS BASED ON C-2-SYMMETRICAL BISOXAZOLINE LIGANDS [J].

BROOKHART, M ;

WAGNER, MI ;

BALAVOINE, GGA ;

HADDOU, HA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) :3641-3642

[5] ENANTIOSELECTIVE CYCLOPOLYMERIZATION OF 1,5-HEXADIENE CATALYZED BY CHIRAL ZIRCONOCENES - A NOVEL STRATEGY FOR THE SYNTHESIS OF OPTICALLY-ACTIVE POLYMERS WITH CHIRALITY IN THE MAIN CHAIN [J].

COATES, GW ;

WAYMOUTH, RM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (01) :91-98

[6] NEW ENANTIOSELECTIVE ROUTES TO BIOLOGICALLY INTERESTING COMPOUNDS [J].

COREY, EJ .

PURE AND APPLIED CHEMISTRY, 1990, 62 (07) :1209-1216

[7] PREPARATION OF MONOMETHYL FUMARATE [J].

DYMICKY, M .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1983, 15 (04) :233-238

[8] Chiral ethylenebis(4,5,6,7-tetrahydro-1-indenyl)zirconium 2,2'-biphenolate. Separation and application to asymmetric polymerization [J].

Habaue, S ;

Sakamoto, H ;

Okamoto, Y .

POLYMER JOURNAL, 1997, 29 (04) :384-386

[9]

HARRIS FW, 1968, MACROMOLECULES, V1, P463

[10] ASYMMETRIC DIELS-ALDER REACTION CATALYZED BY CHIRAL ALKOXYALUMINIUM DICHLORIDE [J].

HASHIMOTO, S ;

KOMESHIMA, N ;

KOGA, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (10) :437-438

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