Microwave-assisted direct synthesis and polymerization of chiral acrylamide

被引：37

作者：

Iannelli, M ^{[1
]}

Ritter, H ^{[1
]}

机构：

[1] Univ Dusseldorf, Inst Organ & Makromol Chem OC2, D-40225 Dusseldorf, Germany

来源：

MACROMOLECULAR CHEMISTRY AND PHYSICS | 2005年 / 206卷 / 03期

关键词：

acrylamides; chiral polymers; microwave irradiation; radical polymerization;

D O I：

10.1002/macp.200400422

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

Chiral (R)-N-(1-phenylethyl)-acryamide (3) was synthesized directly from acrylic acid (1) and (R)-1-phenylethylamine (2) via microwave irradation without any further activation and in a solvent-free medium. The kinetic measurements performed show high selectivity and conversion to the amide after only few minutes of reaction time. It was possible to obtain optically active polymers containing both acrymaide and imide structural units in a one-pot reaction starting from acrylic acid (1), amine (2) and AIBN as a free radical initiator. The same reactions were evaluated by classical thermal heating in an oil bath and the results are compared. [GRAPHIC] The condensation reaction between acrylic acid and (R)-1-phenylenthyamine by MW irradiation in the presence and absence of AIBN as a free radical initiator.

引用

页码：349 / 353

页数：5

共 21 条

[1]

BATTENSTEIN B, 1986, MAKROMOL CHEM-RAPID, V7, P767

[2]

Braun D., 2001, Polymer Synthesis: Theory and Practice, Fundamentals, Methods, Experiments

[3]

Chia HL, 1996, J POLYM SCI POL CHEM, V34, P2087, DOI 10.1002/(SICI)1099-0518(199608)34:11<2087::AID-POLA1>3.0.CO

[4]

2-X

[5] Chiral architectures from macromolecular building blocks [J].

Cornelissen, JJLM ;

Rowan, AE ;

Nolte, RJM ;

Sommerdijk, NAJM .

CHEMICAL REVIEWS, 2001, 101 (12) :4039-4070

[6] Green polymer chemistry: Microwave-assisted single-step synthesis of various (meth)acrylamides and poly(meth)acrylamides directly from (meth)acrylic acid and amines [J].

Goretzki, C ;

Krlej, A ;

Steffens, C ;

Ritter, H .

MACROMOLECULAR RAPID COMMUNICATIONS, 2004, 25 (03) :513-516

[7] Synthesis and characterization of (R)-(+)-α-methylbenzylmethacryloylamine.: A novel and versatile monomer [J].

Gutiérrez-Pérez, R ;

Percino, MJ ;

Chapela, VM ;

Alvarez, C .

DESIGNED MONOMERS AND POLYMERS, 1999, 2 (01) :103-107

[8]

Hayes B.L., 2002, MICROWAVE SYNTHESIS

[9] Soapless emulsion polymerization of butyl methacrylate through microwave heating [J].

He, WD ;

Pan, CY ;

Lu, T .

JOURNAL OF APPLIED POLYMER SCIENCE, 2001, 80 (13) :2455-2459

[10]

IANNELLI M, 2004, IN PRESS TETRAHEDRON

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