Thienothiophenes .2. Synthesis, metallation and bromine->lithium exchange reactions of thieno[3,2-b]thiophene and its polybromo derivatives

被引:125
作者
Fuller, LS
Iddon, B
Smith, KA
机构
[1] SYNTHET CHEM LTD,WOLVERHAMPTON WV10 7BP,ENGLAND
[2] UNIV SALFORD,SCI RES INST,DIV CHEM SCI,SALFORD M5 4WT,LANCS,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 22期
关键词
D O I
10.1039/a701877k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Methods for the large-scale synthesis of thieno[3,2-b]thiophene [including a catalytic vapour-phase reaction (at 550 degrees C) between 2-(2-thienyl)ethanol and carbon disulfide], its 2-carboxylic acid and its 3,6-dibromo and 2,3,5,6-tetrabromo derivatives are reported, With 2 mol equiv. of butyllithium thieno[3,2-b]thiophene gives its 2,5-dilithiated derivative and its 3,6-dibromo derivative gives the 3,6-dilithiated compound, By quenching with suitable electrophilic reagents these dilithiated compounds have been converted into various 2,5- or 3,6-disubstituted thieno[3,2-b]thiophenes, respectively, Likewise 2,3,5,6-tetrabromothieno[3,2-b]thiophene has been converted into 2,5-disubstituted 3,6-dibromothieno[3,2-b]thiophenes.
引用
收藏
页码:3465 / 3470
页数:6
相关论文
共 68 条
  • [1] AZOLES .9. SYNTHESIS OF DERIVATIVES OF THIENO[2,3-D]THIAZOLE, 4H-PYRROLO-[2,3-D]THIAZOLE, 2H-PYRAZOLO[3,4-D]THIAZOLE AND ISOXAZOLO[3,4-D]THIAZOLE FROM THIAZOLIDINE-2,4-DIONE
    ATHMANI, S
    FARHAT, MF
    IDDON, B
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (08): : 973 - 977
  • [2] BARKER JM, 1986, THIOPHENE ITS DERI 3, P565
  • [3] STRUCTURAL BASIS FOR SEMICONDUCTING AND METALLIC POLYMER DOPANT SYSTEMS
    BAUGHMAN, RH
    BREDAS, JL
    CHANCE, RR
    ELSENBAUMER, RL
    SHACKLETTE, LW
    [J]. CHEMICAL REVIEWS, 1982, 82 (02) : 209 - 222
  • [4] Chalcogens as electron donors for selected nonlinear optic phores
    Blenkle, M
    Boldt, P
    Brauchle, C
    Grahn, W
    Ledoux, I
    Nerenz, H
    Stadler, S
    Wichern, J
    Zyss, J
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, (07): : 1377 - 1384
  • [5] Boldt P., 1994, Nonlinear Optics, Principles, Materials, Phenomena and Devices, V8, P173
  • [6] Tricyanoquinodimethane derivatives with extremely large second-order optical nonlinearities
    Boldt, P
    Bourhill, G
    Brauchle, C
    Jim, Y
    Kammler, R
    Muller, C
    Rase, J
    Wichern, J
    [J]. CHEMICAL COMMUNICATIONS, 1996, (06) : 793 - 795
  • [7] BUGGE A, 1973, CHEM SCRIPTA, V3, P190
  • [8] METALATION OF THIENO[2,3-B]THIOPHENE AND THIEN/(3,2-B]THIOPHENE WITH BUTYLLITHIUM
    BUGGE, A
    [J]. ACTA CHEMICA SCANDINAVICA, 1968, 22 (01): : 63 - &
  • [9] PREPARATION OF SOME METHYLTHIENO[2,3-B]-THIOPHENES AND FORMYLTHIENO[2,3-B]-THIOPHENES AND THIENO[3,2-B]THIOPHENES
    BUGGE, A
    [J]. ACTA CHEMICA SCANDINAVICA, 1971, 25 (01): : 27 - &
  • [10] PREPARATION OF SOME BROMINATED THIENO [2,3-B] THIOPHENES AND THIENO [3,2-B] THIOPHENES
    BUGGE, A
    [J]. ACTA CHEMICA SCANDINAVICA, 1969, 23 (08): : 2704 - &