Theoretical Studies on N-O or N-N Bond Formation from Aryl Azide Catalyzed by Iron(II) Bromide Complex

被引:11
|
作者
Li, Juan [1 ]
Zhang, Qi [1 ]
Zhou, Lixin [1 ]
机构
[1] Jinan Univ, Dept Chem, Guangzhou 510632, Guangdong, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 05期
关键词
NEIGHBORING GROUP; PYROLYSIS; DERIVATIVES; RATES; INHIBITORS; 2-AZIDOBENZOPHENONES; HETEROCYCLES; THERMOLYSIS; MECHANISM; CARBONYL;
D O I
10.1021/jo202646t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
DFT calculations have been carried out to study the reaction mechanism on N-O or N-N bond formation from aryl azide catalyzed by iron(II) bromide complex. A favorable reaction pathway is proposed to account for the construction of the core structure of 2H-indazoles or 2,1-benzisoxazoles.
引用
收藏
页码:2566 / 2570
页数:5
相关论文
共 50 条
  • [1] Intramolecular Fe(II)-Catalyzed N-O or N-N Bond Formation from Aryl Azides
    Stokes, Benjamin J.
    Vogel, Carl V.
    Urnezis, Linda K.
    Pan, Minjie
    Driver, Tom G.
    ORGANIC LETTERS, 2010, 12 (12) : 2884 - 2887
  • [2] Copper-Catalyzed N-N Bond Formation by Homocoupling of Ketoximes via N-O Bond Cleavage: Facile, Mild, and Efficient Synthesis of Azines
    Zhao, Mi-Na
    Liang, Hao
    Ren, Zhi-Hui
    Guan, Zheng-Hui
    SYNTHESIS-STUTTGART, 2012, 44 (10): : 1501 - 1506
  • [3] The Mechanism of N-N Double Bond Cleavage by an Iron(II) Hydride Complex
    Bellows, Sarina M.
    Arnet, Nicholas A.
    Gurubasavaraj, Prabhuodeyara M.
    Brennessel, William W.
    Bill, Eckhard
    Cundari, Thomas R.
    Holland, Patrick L.
    Journal of the American Chemical Society, 2016, 138 (37): : 12112 - 12123
  • [4] The Mechanism of N-N Double Bond Cleavage by an Iron(II) Hydride Complex
    Bellows, Sarina M.
    Arnet, Nicholas A.
    Gurubasavaraj, Prabhuodeyara M.
    Brennessel, William W.
    Bilks, Eckhard
    Cundari, Thomas R.
    Holland, Patrick L.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (37) : 12112 - 12123
  • [5] IODOBENZENE DIACETATE-PROMOTED N-N AND N-O BOND FORMATION FOR PYRAZOLO- AND ISOXAZOLOPYRIMIDINE SYNTHESES
    Monguchi, Yasunari
    Hattori, Kazuyuki
    Maegawa, Tomohiro
    Hirota, Kosaku
    Sajiki, Hironao
    HETEROCYCLES, 2009, 79 : 669 - 680
  • [6] Theoretical study of the mechanism for the sequential N-O and N-N bond cleavage within N2O adducts of N-heterocyclic carbenes by a vanadium(III) complex
    Robinson, Robert, Jr.
    Shaw, Miranda F.
    Stranger, Robert
    Yates, Brian F.
    DALTON TRANSACTIONS, 2016, 45 (03) : 1047 - 1054
  • [7] REACTION OF TRIMETHYLSILYL AZIDE WITH C=N-O BOND
    NISHIYAMA, K
    MIYATA, I
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1985, 58 (08) : 2419 - 2420
  • [8] GENERALITY OF REGROUPINGS WITH RUPTURE OF N-N OR N-O BONDS AND WITH FORMATION OF NITRYL GROUP
    GRANDBERG, II
    NAUMOV, IA
    KOST, AN
    DOKLADY AKADEMII NAUK SSSR, 1963, 149 (04): : 838 - &
  • [9] Sequential N-O and N-N Bond Cleavage of N-Heterocyclic Carbene-Activated Nitrous Oxide with a Vanadium Complex
    Tskhovrebov, Alexander G.
    Solari, Euro
    Wodrich, Matthew D.
    Scopelliti, Rosario
    Severin, Kay
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (03) : 1471 - 1473
  • [10] Rhodium mediated N-O bond formation
    Burke, HM
    Gallagher, JF
    Indelli, MT
    Scandola, F
    Vos, JG
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2002, (04) : 846 - 849