Monoaza[5]helicenes. Part 2: Synthesis, characterisation and theoretical calculations

被引：68
作者：
Abbate, S
Bazzini, C
Caronna, T
Fontana, F
Gambarotti, C
Gangemi, F
Longhi, G
Mele, A
Natali Sora, I
Panzeri, W
机构：
[1] Univ Bergamo, Dipartimento Ingn Ind, I-24044 Dalmine, Italy
[2] Univ Brescia, Dipartimento Sci Biomed & Biotecnol, I-25123 Brescia, Italy
[3] Politecn, Dipartimento Chim Mat & Ingn Chim Giulio Natta, I-20131 Milan, Italy
[4] CNR, Ist Chim Riconascimento Mol, Milan, Italy
来源：
TETRAHEDRON | 2006年 / 62卷 / 01期
关键词：
helical structures; helicenes; molecular orbital calculations; photochemistry;
D O I：
10.1016/j.tet.2005.09.132
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of four different monoaza[5]helicenes is reported, to complete the whole series of these compounds, so that systematic studies on their properties can be carried out. They were fully characterised via NMR. A theoretical approach to explain why ring closure occurs to give the most crowded compound is reported, in comparison with earlier calculation methods. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：139 / 148
页数：10
相关论文
共 44 条
  • [1] AuBr3- and Cu(OTf)2-catalyzed intramolecular [4+2] cycloaddition of tethered alkynyl and alkenyl enynones and enynals:: A new synthetic method for functionalized polycyclic hydrocarbons
    Asao, N
    Sato, K
    Menggenbateer
    Yamamoto, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) : 3682 - 3685
  • [2] BARTON JW, 1978, TETRAHEDRON LETT, P1005
  • [3] Synthesis and characterization of some Aza[5]helicenes
    Bazzini, C
    Brovelli, S
    Caronna, T
    Gambarotti, C
    Giannone, M
    Macchi, P
    Meinardi, F
    Mele, A
    Panzeri, W
    Recupero, F
    Sironi, A
    Tubino, R
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (07) : 1247 - 1257
  • [4] DETERMINATION OF ABSOLUTE CONFIGURATION OF (+)-PENTAHELICENE
    BESTMANN, HJ
    BOTH, W
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1972, 11 (04) : 296 - &
  • [5] REARRANGEMENTS OF N-OXIDES - A NOVEL SYNTHESIS OF PYRIDYL CARBINOLS AND ALDEHYDES
    BOEKELHEIDE, V
    LINN, WJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (05) : 1286 - 1291
  • [6] Breitmaier E., 1993, STRUCTURE ELUCIDATIO
  • [7] Caronna T, 2002, HELV CHIM ACTA, V85, P1
  • [8] Enantiopure dihydro-[5]-helicenequinones via Diels-Alder reactions of vinyl dihydrophenanthrenes and (SS)-2-(p-tolylsulfinyl)-1,4-benzoquinone
    Carreño, MC
    García-Cerrada, S
    Urbano, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (32) : 7929 - 7930
  • [9] Self-assembly of disk-shaped molecules to coiled-coil aggregates with tunable helicity
    Engelkamp, H
    Middelbeek, S
    Nolte, RJM
    [J]. SCIENCE, 1999, 284 (5415) : 785 - 788
  • [10] Orientation of chiral heptahelicene C30H18 on copper surfaces:: An x-ray photoelectron diffraction study
    Fasel, R
    Cossy, A
    Ernst, KH
    Baumberger, F
    Greber, T
    Osterwalder, J
    [J]. JOURNAL OF CHEMICAL PHYSICS, 2001, 115 (02) : 1020 - 1027
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