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
  • [31] REACTION OF TERT-BUTOXYL RADICALS WITH ELECTRON-RICH ALPHA-METHYLVINYL MONOMERS
    GRANT, RD
    RIZZARDO, E
    SOLOMON, DH
    MAKROMOLEKULARE CHEMIE-MACROMOLECULAR CHEMISTRY AND PHYSICS, 1984, 185 (09): : 1809 - 1817
  • [32] REACTIONS OF OXYGENATED RADICALS IN THE GAS-PHASE .13. REACTIONS OF TERT-BUTOXYL RADICALS WITH ALKANES AND ALKENES
    SWAY, MI
    WADDINGTON, DJ
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1984, (01): : 63 - 69
  • [33] UNEXPECTED PRODUCTS FROM THE REACTION OF TERT-BUTOXYL RADICALS WITH ACETYLENES IN THE PRESENCE OF AN AMINOXYL RADICAL SCAVENGER
    BOTTLE, S
    BUSFIELD, WK
    JENKINS, ID
    SKELTON, BW
    WHITE, AH
    RIZZARDO, E
    SOLOMON, DH
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1991, (07): : 1001 - 1007
  • [34] tert-Butoxyl radicals generate mainly 7,8-dihydro-8-oxoguanine in DNA
    Mahler, HC
    Schulz, I
    Adam, W
    Grimm, GN
    Saha-Möller, CR
    Epe, B
    MUTATION RESEARCH-DNA REPAIR, 2001, 461 (04): : 289 - 299
  • [35] MEASUREMENT OF HAMMETT RHO-VALUES FOR HOMOLYTIC REACTIONS BY ELECTRON-SPIN RESONANCE SPECTROSCOPY - REACTION OF TERT-BUTOXYL RADICALS WITH SUBSTITUTED ANISOLES
    DAVIES, AG
    QUINTARD, JP
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1978, (11): : 1163 - 1167
  • [36] Hydrogen atom abstraction from resveratrol and two lipophilic derivatives by tert-butoxyl radicals.: A laser flash photolysis study
    Petralia, S
    Spatafora, C
    Tringali, C
    Foti, MC
    Sortino, S
    NEW JOURNAL OF CHEMISTRY, 2004, 28 (12) : 1484 - 1487
  • [37] SYNTHESIS OF INDOLE-DERIVATIVES SUBSTITUTED AT POSITION 7
    KIM, PT
    GUILARD, R
    SAMRETH, S
    SORNAY, R
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1981, 18 (07) : 1373 - 1377
  • [38] INDOLE-DERIVATIVES .126. SUBSTITUTED NITROTRYPTAMINES
    VINOGRAD, LH
    SUVOROV, NN
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1984, (09): : 1206 - 1210
  • [39] HOMOLYTIC ORGANOMETALLIC REACTIONS .11. REACTIONS OF TERT-BUTOXYL RADICALS AND OF KETONE TRIPLETS WITH ORGANOTIN COMPOUNDS
    DAVIES, AG
    SCAIANO, JC
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1973, (13): : 1777 - 1780
  • [40] LINEAR FREE-ENERGY RELATIONSHIPS IN RADICAL REACTIONS .2. HYDROGEN ABSTRACTION FROM SUBSTITUTED TOLUENES BY TERT-BUTYL, TERT-BUTOXYL AND TERT-BUTYLPEROXYL RADICALS
    HEBERGER, K
    JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1994, 7 (05) : 244 - 250