NMR Studies on 1,3-Dipolar Cycloaddition of Nitrile Oxides to Norbornenes

被引:11
|
作者
Gucma, Miroslaw [1 ]
Golebiewski, W. Marek [1 ]
Krawczyk, Maria [1 ]
机构
[1] Inst Ind Organ Chem, PL-03236 Warsaw, Poland
关键词
1,3-dipolar cycloaddition; norbornenes; nitrile oxides; 2D NMR; ADDITIONS;
D O I
10.5935/0103-5053.20130106
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The 1,3-dipolar cycloaddition reaction of nitrile oxides to norbornenes substituted with an acrylate-derived moiety was examined. Only adducts to norbornene system were formed with a good exo selectivity and complete site-selectivity. Structures of the products were elucidated by an extensive application of electrospray ionization-mass spectrometry (ESI-MS) and 2D H-1 and C-13 nuclear magnetic resonance (NMR).
引用
收藏
页码:805 / +
页数:25
相关论文
共 50 条
  • [31] Asymmetric 1,3-dipolar cycloaddition of nitrile oxides with optically active vinylboronic ester
    姜标
    张翱
    阚颖
    [J]. Chinese Journal of Chemistry, 1999, (03) : 293 - 299
  • [32] REVERSING THE REGIOCHEMICAL COURSE OF 1,3-DIPOLAR CYCLOADDITION OF NITRILE OXIDES BY MODIFICATION OF DIPOLAROPHILES
    KAMIMURA, A
    HORI, K
    [J]. TETRAHEDRON, 1994, 50 (27) : 7969 - 7980
  • [33] 1,3-Dipolar cycloadditions of acridine with nitrile oxides
    Corsaro, A
    Pistara, V
    Rescifina, A
    Romeo, G
    Romeo, R
    Chiacchio, U
    [J]. ARKIVOC, 2002, : 5 - 15
  • [34] Intramolecular 1,3-dipolar cycloaddition of cyclo-1,3-diene-tethered nitrile oxides
    Yeh, MCP
    Jou, CF
    Yeh, WT
    Chiu, DY
    Reddy, NRK
    [J]. TETRAHEDRON, 2005, 61 (02) : 493 - 500
  • [35] 1,3-dipolar cycloaddition reactions of nitrile oxides to prop-1-ene-1,3-sultone
    Tian, L
    Xu, GY
    Ye, Y
    Liu, LZ
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2003, 40 (06) : 1071 - 1074
  • [36] 1,3-DIPOLAR CYCLOADDITION OF CARBON DISULFIDE TO A NITRILE OXIDE
    FOYE, WO
    KAUFFMAN, JM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (07): : 2417 - &
  • [37] 1,3-DIPOLAR CYCLOADDITION REACTIONS OF NITRILE OXIDES AND NITRILE IMINES WITH 2-METHOXYVINYL PHENYL KETONE
    COUTOULIARGYROPOULOU, E
    THESSALONIKEOS, E
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (02) : 429 - 432
  • [38] Asymmetric 1,3-Dipolar Cycloaddition of Nitrile Oxides to Chiral Acryloyl Esters BearingGlucofuranose as Auxiliary
    张翱
    姜标
    [J]. 厦门大学学报(自然科学版), 1999, (S1) : 174 - 174
  • [39] 1,3-dipolar cycloaddition reactions of nitrile-N-oxides with o-benzoquinones
    Nair, V
    Radhakrishnan, KV
    Sheela, KC
    Rath, NP
    [J]. TETRAHEDRON, 1999, 55 (49) : 14199 - 14210
  • [40] Asymmetric 1,3-dipolar cycloaddition of nitrile oxides generated in situ by direct oxidation of aldoximes
    Tsuji, M
    Ukaji, Y
    Inomata, K
    [J]. CHEMISTRY LETTERS, 2002, (11) : 1112 - 1113