Synthesis of 3,4'-dibromo-2,2'-bithiophene: A useful intermediate for 3,4'-disubstituted 2,2'-bithiophenes. X-ray molecular structure of 3,4'-dibromo-2,2'-bithiophene

被引:22
作者
Antolini, L [1 ]
Goldoni, F [1 ]
Iarossi, D [1 ]
Mucci, A [1 ]
Schenetti, L [1 ]
机构
[1] UNIV MODENA, DIPARTIMENTO CHIM, I-41100 MODENA, ITALY
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 13期
关键词
D O I
10.1039/a700811b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first synthesis of 3,4'-dibromo-2,2'-bithiophene via metal-catalysed cross-coupling between a metallated and a halogenated thiophene derivative is described. An X-ray crystal structure of 3,4'-dibromo-2,2'-bithiophene is reported, 3,4'-Dibromo-2,2'-bithiophene was converted into corresponding bis(alkylsulfanyl) derivatives through bromine-lithium exchange, followed by reaction with two dialkyl disulfides (Me2S2 or Bu2S2). The H-1 and C-13 NMR data are discussed.
引用
收藏
页码:1957 / 1961
页数:5
相关论文
共 51 条
[1]   ELECTROLUMINESCENCE FROM SUBSTITUTED POLY(THIOPHENES) - FROM BLUE TO NEAR-INFRARED [J].
ANDERSSON, MR ;
BERGGREN, M ;
INGANAS, O ;
GUSTAFSSON, G ;
GUSTAFSSONCARLBERG, JC ;
SELSE, D ;
HJERTBERG, T ;
WENNERSTROM, O .
MACROMOLECULES, 1995, 28 (22) :7525-7529
[2]  
[Anonymous], 1978, INTERPRETATION CARBO
[3]  
ANTOLINI L, UNPUB
[4]   ELECTROCHEMICAL AND OPTICAL-PROPERTIES OF POLY(3-METHYLTHIOPHENES) ELECTROSYNTHESIZED BY 3,3'-4,4'-DIMETHYL-2,2'-BITHIOPHENES, 3,4'-4,4'-DIMETHYL-2,2'-BITHIOPHENES AND 4,4'-DIMETHYL-2,2'-BITHIOPHENES [J].
ARBIZZANI, C ;
BARBARELLA, G ;
BONGINI, A ;
MASTRAGOSTINO, M ;
ZAMBIANCHI, M .
SYNTHETIC METALS, 1992, 52 (03) :329-339
[5]   THE DEFORMABILITY OF THE THIOPHENE RING - A KEY TO THE UNDERSTANDING OF THE CONFORMATIONAL PROPERTIES OF OLIGOPHENES AND POLYTHIOPHENES [J].
BARBARELLA, G ;
ZAMBIANCHI, M ;
BONGINI, A ;
ANTOLINI, L .
ADVANCED MATERIALS, 1993, 5 (11) :834-838
[6]   Polyhydroxyoligothiophenes .2. Hydrogen-bonding-oriented solid state conformation of 3,3'-bis(2-hydroxyethyl)-2,2'-bithiophene and regioselective synthesis of the corresponding head-to-head/tail-to-tail quater- and sexithiophene [J].
Barbarella, G ;
Zambianchi, M ;
Bongini, A ;
Antolini, L .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) :4708-4715
[7]   FROM FUNCTIONALIZED POLYTHIOPHENES TO OLIGOMERS WITH A DEFINED STRUCTURE [J].
BAUERLE, P ;
GOTZ, G ;
SEGELBACHER, U ;
HUTTENLOCHER, D ;
MEHRING, M .
SYNTHETIC METALS, 1993, 57 (2-3) :4768-4776
[8]   SYNTHESIS AND STRUCTURAL CHARACTERIZATION OF ALKYL OLIGOTHIOPHENES - THE 1ST ISOMERICALLY PURE DIALKYLSEXITHIOPHENE [J].
BAUERLE, P ;
PFAU, F ;
SCHLUPP, H ;
WURTHNER, F ;
GAUDL, KU ;
CARO, MB ;
FISCHER, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (03) :489-494
[9]   OLIGOTHIOPHENES - YET LONGER - SYNTHESIS, CHARACTERIZATION, AND SCANNING-TUNNELING-MICROSCOPY IMAGES OF HOMOLOGOUS, ISOMERICALLY PURE OLIGO(ALKYLTHIOPHENE)S [J].
BAUERLE, P ;
FISCHER, T ;
BIDLINGMEIER, B ;
STABEL, A ;
RABE, JP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (03) :303-307
[10]  
Bauerle P, 1996, LIEBIGS ANN-RECL, P279