On the Phosphite-Mediated Synthesis of Dithiafulvenes and π-Extended Tetrathiafulvalenes

被引：10
作者：
Schou, Simon Stubbe [1 ]
Parker, Christian Richard [1 ]
Lincke, Kasper [1 ]
Jennum, Karsten [1 ]
Vibenholt, Johan [1 ]
Kadziola, Anders [1 ]
Nielsen, Mogens Brondsted [1 ]
机构：
[1] Univ Copenhagen, Dept Chem, DK-2100 Copenhagen O, Denmark
来源：
SYNLETT | 2013年 / 24卷 / 02期
关键词：
cruciform; heterocycles; phosphite; sulfur; tetrathiafulvalene; TRIALKYL PHOSPHITES; PHTHALIC-ANHYDRIDE; BIPHTHALYL; CONVERSION; ANALOGS; TTF;
D O I：
10.1055/s-0032-1317921
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
By phosphite-mediated couplings between functionalized benzaldehydes and 1,3-dithiole-2-thiones we have obtained a variety of pi-extended tetrathiafulvalenes (TTF). In particular, this method has provided a new stilbene-extended TTF with lateral alkyne functionalities, an H-type cruciform structure. This outcome is the result of a phosphite-mediated coupling between two aldehydes.
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收藏
页码：231 / 235
页数：5
相关论文
共 26 条
  • [1] Synthesis and characterization of extended tetrathiafulvalenes with di-, tri-, and tetraethynylethene cores
    Andersson, AS
    Qvortrup, K
    Torbensen, ER
    Mayer, JP
    Gisselbrecht, JP
    Boudon, C
    Gross, M
    Kadziola, A
    Kilså, K
    Nielsen, MB
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (17) : 3660 - 3671
  • [2] Arbuzov A., 1960, IZV AKAD NAUK USS KN, V54, P1030
  • [3] Conformational control of TTFV π-frameworks through naphthyl substituents
    Bouzan, Stephen
    Chen, Guang
    Mulla, Karimulla
    Dawe, Louise N.
    Zhao, Yuming
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (38) : 7673 - 7676
  • [4] Synthesis and properties of TTFV-hinged molecular tweezers
    Chen, Guang
    Bouzan, Stephen
    Zhao, Yuming
    [J]. TETRAHEDRON LETTERS, 2010, 51 (50) : 6552 - 6556
  • [5] Thiolated π-extended tetrathiafulvalenes:: Versatile multifunctional π-systems
    Christensen, Christian A.
    Batsanov, Andrei S.
    Bryce, Martin R.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) : 1301 - 1308
  • [6] Electropolymerization of triphenylamine-dithiafulvene hybrid extended pi-conjugated systems
    Cocherel, Nicolas
    Leriche, Philippe
    Ripaud, Emilie
    Gallego-Planas, Nuria
    Frere, Pierre
    Roncali, Jean
    [J]. NEW JOURNAL OF CHEMISTRY, 2009, 33 (04) : 801 - 806
  • [7] Synthesis strategies and chemistry of nonsymmetrically substituted tetrachalcogenafulvalenes
    Fabre, JM
    [J]. CHEMICAL REVIEWS, 2004, 104 (11) : 5133 - 5150
  • [8] TETRATHIAFULVALENE-SUBSTITUTED AND DITHIAFULVENE-SUBSTITUTED MESITYLENES, NEW PI-DONOR MOLECULES WITH 3-FOLD SYMMETRY AND THE FORMATION OF AN UNPRECEDENTED NEW CLASS OF ELECTROACTIVE POLYMERS
    FOURMIGUE, M
    JOHANNSEN, I
    BOUBEKEUR, K
    NELSON, C
    BATAIL, P
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (09) : 3752 - 3759
  • [9] New redox active ligands involving a tetrathiafulvalene vinylogue backbone
    Guerro, Michel
    Pham, Ngoc Ha
    Massue, Julien
    Bellec, Nathalie
    Lorcy, Dominique
    [J]. TETRAHEDRON, 2008, 64 (22) : 5285 - 5290
  • [10] Synthesis and properties of new tetrathiapentalene donors composed of vinylogous TTFs
    Iwamoto, Shintaro
    Watanabe, Shunsuke
    Fueno, Hiroyuki
    Tanaka, Kazuyoshi
    Misaki, Yohji
    [J]. CHEMISTRY LETTERS, 2008, 37 (01) : 82 - 83
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