Silyl-substituted tetrathia[7]helicenes: Synthesis, X-ray characterization and reactivity

被引：35
作者：
Bossi, Alberto
Maiorana, Stefano
Graiff, Claudia
Tiripicchio, Antonio
Licandro, Emanuela
机构：
[1] Univ Studi Milano, Dept Chim Organ Ind, I-20133 Milan, Italy
[2] Univ Studi Parma, Dipartimento Chim Gen Inorgan Chim Analit, I-43100 Parma, Italy
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 27期
关键词：
C-C coupling; heterohelicenes; sulfur heterocycles; fused-ring systems; olefination;
D O I：
10.1002/ejoc.200700494
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We describe the synthesis of trialkylsilyl- substituted trans1,2-bis(thieno[3,2-e]benzothiophene-2-yl)ethenes as suitable soluble precursors for the preparation of the corresponding silylated tetrathia[7]helicenes, which, in turn, can be desilylated or transformed into dihalogen -substituted derivatives through electrophilic substitution of silyl substituents. X-ray structural studies showed that the presence of the two triiso-propylsilyl groups on the terminal thiophene rings accounts for the high solubility of the alkene and for the very large dihedral angle in the helicene. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).
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收藏
页码：4499 / 4509
页数：11
相关论文
共 51 条
[1]   Monoaza[5]helicenes. Part 2: Synthesis, characterisation and theoretical calculations [J].
Abbate, S ;
Bazzini, C ;
Caronna, T ;
Fontana, F ;
Gambarotti, C ;
Gangemi, F ;
Longhi, G ;
Mele, A ;
Natali Sora, I ;
Panzeri, W .
TETRAHEDRON, 2006, 62 (01) :139-148
[2]  
AKAGAWA H, 1985, J CHEM SOC P1, P1899
[3]   Synthesis and characterization of new hexahelicene derivatives [J].
Aloui, Faouzi ;
El Abed, Riadh ;
Marinetti, Angela ;
Ben Hassine, Bechir .
TETRAHEDRON LETTERS, 2007, 48 (11) :2017-2020
[4]   A novel and efficient approach to (Z)-1,2-bis(benzodithienyl)ethene precursors of tetrathia[7]helicenes [J].
Baldoli, C ;
Bossi, A ;
Giannini, C ;
Licandro, E ;
Maiorana, S ;
Perdicchia, D ;
Schiavo, M .
SYNLETT, 2005, (07) :1137-1141
[5]   Bis(enediyne) macrocycles: Synthesis, reactivity, and structural analysis [J].
Blanchette, HS ;
Brand, SC ;
Naruse, H ;
Weakley, TJR ;
Haley, MM .
TETRAHEDRON, 2000, 56 (49) :9581-9588
[6]   Hyper-Rayleigh scattering of neutral and charged helicenes [J].
Botek, E ;
Spassova, M ;
Champagne, B ;
Asselberghs, I ;
Persoons, A ;
Clays, K .
CHEMICAL PHYSICS LETTERS, 2005, 412 (4-6) :274-279
[7]  
BOTEK E, 2005, J CHEM PHYS, V122
[8]   Asymmetric catalysis in the [2+2+2] cycloaddition of arynes and alkynes:: Enantioselective synthesis of a pentahelicene [J].
Caeiro, Jorge ;
Pena, Diego ;
Cobas, Agustin ;
Perez, Dolores ;
Guitian, Enrique .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) :2466-2474
[9]  
Caronna T, 2002, HELV CHIM ACTA, V85, P1
[10]   Molecular crystal architecture and optical properties of a thiohelicenes series containing 5, 7, 9, and 11 rings prepared via photochemical synthesis [J].
Caronna, T ;
Catellani, M ;
Luzzati, S ;
Malpezzi, L ;
Meille, SV ;
Mele, A ;
Richter, C ;
Sinisi, R .
CHEMISTRY OF MATERIALS, 2001, 13 (11) :3906-3914
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