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.
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页数:6
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共 31 条
  • [21] Enantio- and diastereotopos differentiation in the palladium(II)-catalyzed hydrosilylation of bicyclo[2.2.1]alkene scaffolds with silicon-stereogenic silanes
    Rendler, Sebastian
    Froehlich, Roland
    Keller, Manfred
    Oestreich, Martin
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (15) : 2582 - 2591
  • [22] THE PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOTIN REAGENTS WITH ORGANIC ELECTROPHILES
    STILLE, JK
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (06): : 508 - 523
  • [23] Hinged bis-porphyrin scaffolds I. The synthesis of a new porphyrin diene and its role in constructing hinged porphyrin dyads and cavity systems
    Tang, Hesheng
    Dong, Zemin
    Merican, Zul
    Margetic, Davor
    Marinic, Zeljko
    Gunter, Maxwell J.
    Officer, David
    Butler, Douglas N.
    Warrener, Ronald N.
    [J]. TETRAHEDRON LETTERS, 2009, 50 (06) : 667 - 670
  • [24] Synthesis of 2,3-disubstituted norbornadienes
    Tranmer, GK
    Yip, C
    Handerson, S
    Jordan, RW
    Tam, W
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2000, 78 (05): : 527 - 535
  • [25] Application of a Rhodium-Catalyzed Addition/Cyclization Sequence toward the Synthesis of Polycyclic Heteroaromatics
    Tseng, Nai-Wen
    Lautens, Mark
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (04) : 1809 - 1811
  • [26] High temperature bromination .7. Bromination of norbornadiene
    Tutar, A
    Tagkesenligil, Y
    Cakmak, O
    Abbasoglu, R
    Balci, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) : 8297 - 8300
  • [27] STUDIES OF BENZONORBORNENE AND DERIVATIVES .2. AC-BROMOBENZONORBORNENES AND AC-BROMOBENZONORBORNADIENES
    WILT, JW
    CHENIER, PJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (05) : 1562 - &
  • [28] BICYCLOHEPTADIENE DIBROMIDES
    WINSTEIN, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (06) : 1516 - &
  • [29] Intermolecular, catalytic asymmetric hydroamination of bicyclic alkenes and dienes in high yield and enantioselectivity
    Zhou, Jianrong
    Hartwig, John F.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (37) : 12220 - +
  • [30] Zimmerman H.E., 1980, REARRANGEMENTS GROUN, V3, P131