1,3-DIPOLAR CYCLOADDITIONS TO NITROGEN-SUBSTITUTED ALLENES

被引：49
|
作者：
BROGGINI, G
BRUCHE, L
ZECCHI, G
PILATI, T
机构：
[1] UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,VIA GOLGI 19,I-20133 MILAN,ITALY
[2] CTR STUDIO RELAZ STRUTT & REATT CHIM,CNR,VIA GOLGI 19,I-20133 MILAN,ITALY
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 03期
关键词：
D O I：
10.1039/p19900000533
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of nitrogen-substituted allenes (2a-h) was treated with 3,5-dichloro-2,4,6- trimethylbenzonitrile oxide (4) in boiling tetrachloromethane. The reaction occurred predominantly (or exclusively) at the α,β double bond. Regardless of the site of cycloaddition, the carbon of the nitrite oxide bonded selectively to the central carbon of the aliene. 4-Methylene-4,5-dihydroisoxazole monoadducts (5) reacted further to form spiro-diadducts. The stereochemistry of one diadduct was determined by X-ray diffraction analysis.
引用
收藏
页码：533 / 539
页数：7
相关论文
共 50 条
  • [31] 1,3-DIPOLAR CYCLOADDITIONS OF DIAZOALKANES TO SOME NITROGEN CONTAINING HETEROAROMATIC SYSTEMS
    STANOVNIK, B
    TETRAHEDRON, 1991, 47 (18-19) : 2925 - 2945
  • [32] Microwave-Assisted 1,3-dipolar Cycloadditions to Nitrogen Containing Heterocycles
    Cieslik, Wioleta
    Serda, Maciej
    Musiol, Robert
    CURRENT ORGANIC CHEMISTRY, 2015, 19 (14) : 1410 - 1427
  • [33] 1,3-DIPOLAR CYCLOADDITIONS OF 3,5-DICHLORO-2,4,6-TRIMETHYLBENZONITRILE OXIDE TO PHENOXY-SUBSTITUTED ALLENES
    ZECCHI, G
    JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (15): : 2796 - 2798
  • [34] Theoretical study of 1,3-dipolar cycloadditions of nitrone and fulminic acid with substituted ethylenes
    Magnuson, EC
    Pranata, J
    JOURNAL OF COMPUTATIONAL CHEMISTRY, 1998, 19 (16) : 1795 - 1804
  • [35] DOUBLE 1,3-DIPOLAR CYCLOADDITIONS OF MESOIONIC HETEROCYCLES TO N-SUBSTITUTED MALEIMIDES
    NANYA, S
    KURACHI, Y
    BUTSUGAN, Y
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (08) : 1853 - 1855
  • [36] Carbonyl ylide 1,3-dipolar cycloadditions with porphyrins
    Flemming, J
    Dolphin, D
    TETRAHEDRON LETTERS, 2002, 43 (40) : 7281 - 7283
  • [37] Iridium-Catalyzed 1,3-Dipolar Cycloadditions
    Carmona, Daniel
    Oro, Luis A.
    IRIDIUM CATALYSIS, 2011, 34 : 209 - 229
  • [38] Intermolecular 1,3-dipolar cycloadditions of azomethine imines
    Jones, Raymond C. F.
    Hollis, Stephen J.
    Iley, James N.
    ARKIVOC, 2007, : 152 - 166
  • [39] Regiochemistry of 1,3-dipolar cycloadditions between azides and substituted ethylenes: a theoretical study
    Chandra, AK
    Uchimaru, T
    Nguyen, MT
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (10): : 2117 - 2121
  • [40] Triazol-substituted titanocenes by strain-driven 1,3-dipolar cycloadditions
    Gansaeuer, Andreas
    Okkel, Andreas
    Schwach, Lukas
    Wagner, Laura
    Selig, Anja
    Prokop, Aram
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 : 1630 - 1637
12345