Synthesis and Diels-Alder cycloaddition reaction of norbornadiene and benzonorbornadiene dimers

被引：5
作者：
Nisanci, Bilal [1 ]
Dalkilic, Erdin [1 ]
Guney, Murat [1 ]
Dastan, Arif [1 ]
机构：
[1] Ataturk Univ, Fac Sci, Dept Chem, TR-25240 Erzurum, Turkey
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 5卷
关键词：
benzonorbornadiene; Diels-Alder reaction; norbornadiene; Stille coupling; HIGH-TEMPERATURE BROMINATION; DERIVATIVES; DIENES;
D O I：
10.3762/bjoc.5.39
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Dimeric forms of norbornadiene and benzonorbornadiene were synthesized starting with known monobromide derivatives. The Diels-Alder cycloaddition reaction of dimers with TCNE and PTAD was investigated and new norbornenoid polycyclics were obtained. All compounds were characterized properly using NMR spectroscopy.
引用
收藏
页数：6
相关论文
共 31 条
  • [1] A convenient synthesis of pyridine and 2,2′-bipyridine derivatives
    Altuna-Urquijo, Marta
    Gehre, Alexander
    Stanforth, Stephen P.
    Tarbit, Brian
    [J]. TETRAHEDRON, 2009, 65 (05) : 975 - 984
  • [2] Altundas R, 2002, EUR J ORG CHEM, V2002, P526, DOI 10.1002/1099-0690(20022)2002:3<526::AID-EJOC526>3.0.CO
  • [3] 2-N
  • [4] BARKHASH VA, 1984, TOP CURR CHEM, V116, P1
  • [5] NUCLEOPHILIC EXCHANGE-REACTIONS AT 1-CHLOROQUADRICYCLANE - 1,5-DEHYDROQUADRICYCLANE AND 1,7-DEHYDROQUADRICYCLANE AS REACTIVE INTERMEDIATES
    BAUMGARTEL, O
    SZEIMIES, G
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1983, 116 (06): : 2180 - 2204
  • [6] Chiral polycyclic ketones via desymmetrization of dihaloolefins
    Borsato, Giuseppe
    Linden, Anthony
    De Lucchi, Ottorino
    Lucchini, Vittorio
    Wolstenholme, David
    Zambon, Alfonso
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (11) : 4272 - 4275
  • [7] BRIDGED POLYCYCLIC COMPOUNDS .47. ADDITION OF BROMINE AND CHLORINE TO BENZONORBORNADIENE AND SOME REACTIONS OF RESULTING ADDUCTS
    CRISTOL, SJ
    NACHTIGA.GW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (12) : 3727 - &
  • [8] Novel and versatile protocol for the preparation of functionalized benzocyclotrimers
    Dalkilic, Erdin
    Gueney, Murat
    Dastan, Arif
    Saracoglu, Nurullah
    De Lucchi, Ottorino
    Fabris, Fabrizio
    [J]. TETRAHEDRON LETTERS, 2009, 50 (17) : 1989 - 1991
  • [9] High temperature bromination. Part 18: Bromination of benzonorbornadiene derivatives: Polybrominated benzonorbornenes and benzonorbornadienes
    Dastan, A
    Balci, M
    [J]. TETRAHEDRON, 2005, 61 (23) : 5481 - 5488
  • [10] HIGH-TEMPERATURE BROMINATION .5. FUNCTIONALIZATION OF BENZONORBORNADIENE - HIGH-TEMPERATURE BROMINATION AND ELECTROCHEMICAL OXIDATION
    DASTAN, A
    DEMIR, U
    BALCI, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (22) : 6534 - 6538
1234