An efficient method for the synthesis of 3-alkylthiophenes bearing functional groups on the side chain: imides and amides

被引：10

作者：

Dai, J ^{[1
]}

Sellers, JL ^{[1
]}

Noftle, RE ^{[1
]}

机构：

[1] Wake Forest Univ, Dept Chem, Winston Salem, NC 27109 USA

来源：

SYNTHETIC METALS | 2003年 / 139卷 / 01期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

polythiophenes; 3-thienylalkylimides; 3-thienylalkylamides; Rieke (R) zinc; synthesis; electrochemistry;

D O I：

10.1016/S0379-6779(02)01324-3

中图分类号：

T [工业技术];

学科分类号：

08 ;

摘要：

A method utilizing Rieke(R) zinc reagents is described for the synthesis of 5-(3-thienyl)pentanenitrile from which 5-(3-thienyl)-N-acetylpentanamide and 5-(3-thienyl)-N-(4-trifluoromethyl)benzoylpentaneamine have been prepared. A study of the effect of different catalysts on the product composition and extent of conversion has been carried out. The method should be widely applicable to the synthesis of 3-alkylthiophenes bearing functional groups on the side chain which have been rather difficult to prepare previously. The characterization and oxidative polymerization/oligomerization of the new compounds is described. (C) 2003 Elsevier Science B.V. All rights reserved.

引用

页码：81 / 88

页数：8

共 30 条

[11] SOLUTION AND SOLID-STATE ELECTROCHEMISTRY OF SOLUBLE SUBSTITUTED POLYTHIOPHENES [J].

GUAY, J ;

DIAZ, AF ;

BERGERON, JY ;

LECLERC, M .

JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1993, 361 (1-2) :85-91

[12] DICHLORO[1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE]PALLADIUM-(II) - AN EFFECTIVE CATALYST FOR CROSS-COUPLING OF SECONDARY AND PRIMARY ALKYL GRIGNARD AND ALKYLZINC REAGENTS WITH ORGANIC HALIDES [J].

HAYASHI, T ;

KONISHI, M ;

KOBORI, Y ;

KUMADA, M ;

HIGUCHI, T ;

HIROTSU, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (01) :158-163

[13]

HEADRIDGE JB, 1969, ELECTROCHEMICAL TECH

[14] Conjugated polymers incorporating pendant functional groups - synthesis and characterisation [J].

Higgins, SJ .

CHEMICAL SOCIETY REVIEWS, 1997, 26 (04) :247-257

[15]

LEMAIRE M, 1987, NEW J CHEM, V11, P703

[16] A NOVEL MECHANISM OF ELECTROCHEMICAL DEPOSITION OF CONDUCTING POLYMERS - 2-DIMENSIONAL LAYER-BY-LAYER NUCLEATION AND GROWTH OBSERVED FOR POLY(THIOPHENE-3-ACETIC ACID) [J].

LI, FB ;

ALBERY, WJ .

ELECTROCHIMICA ACTA, 1992, 37 (03) :393-401

[17] Reactive groups on polymer coated electrodes 10. Electrogenerated conducting polyalkylthiophenes bearing activated ester groups [J].

Li, G ;

Kossmehl, C ;

Hunnius, W ;

Zhu, H ;

Kautek, W ;

Plieth, W ;

Melsheimer, J ;

Doblhofer, K .

POLYMER, 2000, 41 (02) :423-432

[18]

Li GT, 1998, MACROMOL CHEM PHYS, V199, P2737

[19]

Randriamahazaka H, 1999, J ELECTROANAL CHEM, V472, P103, DOI 10.1016/S0022-0728(99)00258-2

[20]

Rieke RD, 2000, ALDRICHIM ACTA, V33, P52

← 1 2 3 →