REACTIVITY OF TERT-BUTOXYL RADICALS TOWARDS SUBSTITUTED INDOLE-DERIVATIVES

被引:6
|
作者
ENCINAS, MV [1 ]
LISSI, EA [1 ]
MAJMUD, C [1 ]
OLEA, AF [1 ]
机构
[1] UNIV CHILE,FAC CIENCIAS,DEPT QUIM,SANTIAGO,CHILE
关键词
D O I
10.1002/kin.550230902
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Tert-butoxyl radicals react with indole and methyl substituted derivatives by hydrogen abstraction. For those compounds which are unsubstituted at the N-atom, hydrogen abstraction takes place almost exclusively at the N-H bond. The reactivity of these compounds correlates with their donor electron capacity, pointing to significant contribution of charge transfer to the transition state stability. Substitution at the N atom considerably decreases the reactivity.
引用
收藏
页码:761 / 766
页数:6
相关论文
共 50 条
  • [41] The autoxidation of aliphatic esters. Part 1. The reactions of tert-butoxyl and cumyloxyl radicals with neopentyl esters
    Lindsay Smith, John R.
    Nagatomi, Eiji
    Stead, Angela
    Waddington, David J.
    Bévière, Stéphane D.
    Journal of the Chemical Society. Perkin Transactions 2, 2000, (06): : 1193 - 1198
  • [42] Revealing the Iron-Catalyzed β-Methyl Scission of tert-Butoxyl Radicals via the Mechanistic Studies of Carboazidation of Alkenes
    Chiou, Mong-Feng
    Xiong, Haigen
    Li, Yajun
    Bao, Hongli
    Zhang, Xinhao
    MOLECULES, 2020, 25 (05):
  • [43] The autoxidation of aliphatic esters.: Part 1.: The reactions of tert-butoxyl and cumyloxyl radicals with neopentyl esters
    Smith, JRL
    Nagatomi, E
    Stead, A
    Waddington, DJ
    Bévière, SD
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2000, 6 : 1193 - 1198
  • [44] EFFECTS OF SOLVATION ON THE ENTHALPIES OF REACTION OF TERT-BUTOXYL RADICALS WITH PHENOL AND ON THE CALCULATED O-H BOND STRENGTH IN PHENOL
    WAYNER, DDM
    LUSZTYK, E
    PAGE, D
    INGOLD, KU
    MULDER, P
    LAARHOVEN, LJJ
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (34) : 8737 - 8744
  • [45] Effects of solvation on the enthalpies of reaction of tert-butoxyl radicals with phenol and on the calculated O-H bond strength in phenol
    Wayner, D.D.M.
    Lusztyk, E.
    Page, D.
    Ingold, K.U.
    Mulder, P.
    Laarhoven, L.J.J.
    Aldrich, H.S.
    Journal of the American Chemical Society, 1995, 117 (34):
  • [46] SYNTHESIS AND SPECTRAL CHARACTERIZATION OF 2-SUBSTITUTED INDOLE-DERIVATIVES
    ALAZAWE, S
    SARKIS, GY
    JOURNAL OF CHEMICAL AND ENGINEERING DATA, 1973, 18 (01): : 109 - 111
  • [47] SYNTHESIS AND PHOTOCHEMICAL BEHAVIOR OF SUBSTITUTED ETHYLENES - PYRROLE AND INDOLE-DERIVATIVES
    GALIAZZO, G
    GENNARI, G
    BORTOLUS, P
    GAZZETTA CHIMICA ITALIANA, 1991, 121 (02): : 67 - 71
  • [48] NEW SYNTHETIC PATH TO N-SUBSTITUTED INDOLE-DERIVATIVES
    TAMBUTE, A
    COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES SERIE C, 1974, 278 (20): : 1239 - 1242
  • [49] REACTION OF VINYL-ETHER AND PROPENYL-ETHERS WITH TERT-BUTOXYL RADICALS - AN ELECTRON-SPIN-RESONANCE STUDY
    KORTH, HG
    SUSTMANN, R
    TETRAHEDRON LETTERS, 1985, 26 (21) : 2551 - 2554
  • [50] Reaction of singlet-excited 2,3-diazabicyclo[2.2.2]oct-2-ene and tert-butoxyl radicals with aryl-substituted benzofuranones
    Lundgren, CV
    Koner, AL
    Tinkl, M
    Pischel, U
    Nau, WM
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05): : 1977 - 1983