RING EXPANSION AND REARRANGEMENT REACTIONS OF N-HETEROARYLMETHYL RADICALS

被引:4
|
作者
MCLELLAN, JF [1 ]
MCNAB, H [1 ]
MUIR, TW [1 ]
机构
[1] UNIV EDINBURGH,DEPT CHEM,W MAINS RD,EDINBURGH EH9 3JJ,MIDLOTHIAN,SCOTLAND
关键词
D O I
10.1039/c39930000839
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Flash vacuum pyrolysis of N-(p-chlorophenoxymethyl)azoles (e.g. 2 and 3) gives ring expanded products (e.g. 4 and 8) formed via N-heteroarylmethyl radicals (e.g. 1 and 6); the mechanism of ring expansion generally involves a novel 'walk'-rearrangement of the radical centre.
引用
收藏
页码:839 / 840
页数:2
相关论文
共 50 条
  • [21] β-Aminocarbonates in Regioselective and Ring Expansion Reactions
    Arico, Fabio
    Aldoshin, Alexander S.
    Musolino, Manuele
    Crisma, Marco
    Tundo, Pietro
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (01): : 236 - 243
  • [22] Investigating ring expansion reactions with pentaphenylborole
    Huang, Kexuan
    Martin, Caleb
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
  • [23] RING EXPANSION AND CLEAVAGE REACTIONS OF CYCLODISTANNAZANES
    HANSSGEN, D
    POHL, I
    CHEMISCHE BERICHTE-RECUEIL, 1979, 112 (08): : 2798 - 2803
  • [24] CONSECUTIVE RING-CLOSURE AND NEOPHYL REARRANGEMENT OF SOME ALKENYLARYL RADICALS
    ABEYWICKREMA, AN
    BECKWITH, ALJ
    GERBA, S
    JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18): : 4072 - 4078
  • [25] Highly stereoselective ring expansion reactions mediated by attractive cation-n interactions
    Ribelin, Timothy
    Katz, Christopher E.
    English, Donna G.
    Smith, Sherriel
    Manukyan, Anna K.
    Day, Victor W.
    Neuenswander, Benjamin
    Poutsma, Jennifer L.
    Aube, Jeffrey
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (33) : 6233 - 6235
  • [26] NEW RING FORMATION AND REARRANGEMENT REACTIONS IN THE QUINAZOLINE SERIES
    BAHR, F
    DIETZ, G
    PHARMAZIE, 1979, 34 (5-6): : 364 - 364
  • [27] Unexpected ring contraction and oxidation rearrangement reactions of securinine
    Li, Jun-Yong
    Zhao, Bing-Xin
    Zhang, Wen
    Li, Chen
    Huang, Xiao-Jun
    Wang, Ying
    Sun, Ping-Hua
    Ye, Wen-Cai
    Chen, Wei-Min
    TETRAHEDRON, 2012, 68 (21) : 3972 - 3979
  • [28] Ring-expansion of an aziridinone to a hexahydrotriazine involving a novel rearrangement
    Yusoff, MM
    Talaty, ER
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 214 : 191 - ORGN
  • [29] HOMOLYTIC RING FISSION REACTIONS OF CYCLOALKYLMETHYL AND BICYCLOALKYL RADICALS
    BEWS, JR
    GLIDEWELL, C
    WALTON, JC
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1982, (11): : 1447 - 1453
  • [30] THE RING-OPENING REACTIONS OF CYCLOBUTYLMETHYL AND CYCLOBUTENYLMETHYL RADICALS
    INGOLD, KU
    MAILLARD, B
    WALTON, JC
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1981, (06): : 970 - 974