Transition metal catalyzed ring opening reactions of 2-phenyl-3-vinyl substituted 2H-azirines

被引:57
|
作者
Padwa, A [1 ]
Stengel, T [1 ]
机构
[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA
基金
美国国家科学基金会;
关键词
D O I
10.1016/j.tetlet.2004.06.046
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of 2-phenyl-3-vinyl-substituted 2H-azirines with Grubbs' catalyst induces a clean rearrangement and affords products derived from carbon-nitrogen bond cleavage of the 2H-azirine ring. However, when the reaction was carried Out using Wilkinson's catalyst in an alcoholic solvent, the only product obtained in high yield corresponded to an alpha,beta-tinsaturated oxime. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5991 / 5993
页数:3
相关论文
共 50 条
  • [21] THERMAL TRANSFORMATION OF ALLYL SUBSTITUTED 2H-AZIRINES TO PYRIDINES
    PADWA, A
    CARLSEN, PHJ
    TETRAHEDRON LETTERS, 1978, (05) : 433 - 436
  • [22] INTRAMOLECULAR DIPOLAR CYCLOADDITION REACTIONS OF UNSATURATED 2H-AZIRINES
    PADWA, A
    KAMIGATA, N
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (06) : 1871 - 1880
  • [23] Kinetic Resolution of 2H-Azirines by Asymmetric Allylation Reactions
    Pan, Yu-Liang
    Shao, Ying-Bo
    Wang, Jie
    Liu, Zhen
    Chen, Li
    Li, Xin
    ACS CATALYSIS, 2021, 11 (22) : 13752 - 13760
  • [24] Regioselective Transition Metal-Free Catalytic Ring Opening of 2H-Azirines by Phenols and Naphthols; One-Pot Access to Benzo- and Naphthofurans
    Roy, Arnab
    Biswas, Subrata
    Duari, Surajit
    Maity, Srabani
    Mishra, Abhishek Kumar
    de Souza, Aguinaldo R.
    Elsharif, Asma M.
    Morgon, Nelson H.
    Biswas, Srijit
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (22): : 15580 - 15588
  • [25] ZnCl2-Catalyzed [3+2] Cycloaddition of Benzimidates and 2H-Azirines for the Synthesis of Imidazoles
    Shi, Shoujie
    Xu, Kang
    Jiang, Cheng
    Ding, Zhenhua
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (23): : 14791 - 14796
  • [26] Copper-catalyzed asymmetric reductions of aryl 2H-azirines
    Palchak, Zachary L.
    Unger, John B.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [27] Ruthenium-Catalyzed Synthesis of 2H-Azirines from Isoxazolinones
    Rieckhoff, Stefan
    Titze, Marvin
    Frey, Wolfgang
    Peters, Rene
    ORGANIC LETTERS, 2017, 19 (17) : 4436 - 4439
  • [28] Copper-Catalyzed Diazidation of Allenes: Access to 3-(Azidomethyl)-2H-Azirines
    Zhang, Shen-Yuan
    Hu, Li-Yan
    Li, Yang
    Li, Yuan
    Luo, Kai
    Wu, Lei
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (03) : 444 - 449
  • [29] Fe(II)-Catalyzed Amination of Aromatic C-H Bonds via Ring Opening of 2H-Azirines: Synthesis of 213-Disubstituted Indoles
    Jana, Samaresh
    Clements, Mack D.
    Sharp, Barry K.
    Zheng, Nan
    ORGANIC LETTERS, 2010, 12 (17) : 3736 - 3739
  • [30] EVIDENCE FOR VINYL NITRENE INTERMEDIATES IN THE THERMAL REARRANGEMENT OF 2H-AZIRINES INTO INDOLES
    ISOMURA, K
    AYABE, GI
    HATANO, S
    TANIGUCHI, H
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (24) : 1252 - 1253