Reactivity of phthalimide N-oxyl radical (PINO) toward the phenolic O-H bond.: A kinetic study

被引:40
作者
Baciocchi, E
Gerini, MF
Lanzalunga, O
机构
[1] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy
[2] Univ Roma La Sapienza, IMC, CNR, Sez Meccanismi Reaz, I-00185 Rome, Italy
关键词
D O I
10.1021/jo048656o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reactivity of the phthalimide N-oxyl radical (PINO) toward the OH bond of a series of substituted phenols was kinetically investigated in CH3CN. The reaction selectivity and the deuterium kinetic isotope effect were determined. Information on the kinetic solvent effect was also obtained with phenol as the substrate.
引用
收藏
页码:8963 / 8966
页数:4
相关论文
共 37 条
  • [1] HYDROGEN-BONDING .7. A SCALE OF SOLUTE HYDROGEN-BOND ACIDITY BASED ON LOG K-VALUES FOR COMPLEXATION IN TETRACHLOROMETHANE
    ABRAHAM, MH
    GRELLIER, PL
    PRIOR, DV
    DUCE, PP
    MORRIS, JJ
    TAYLOR, PJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (06): : 699 - 711
  • [2] HYDROGEN-BONDING .10. A SCALE OF SOLUTE HYDROGEN-BOND BASICITY USING LOG K VALUES FOR COMPLEXATION IN TETRACHLOROMETHANE
    ABRAHAM, MH
    GRELLIER, PL
    PRIOR, DV
    MORRIS, JJ
    TAYLOR, PJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1990, (04): : 521 - 529
  • [3] Hydroxylamines as oxidation catalysts: Thermochemical and kinetic studies
    Amorati, R
    Lucarini, M
    Mugnaini, V
    Pedulli, GF
    Minisci, F
    Recupero, F
    Fontana, F
    Astolfi, P
    Greci, L
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) : 1747 - 1754
  • [4] Aerobic oxidation of benzyl alcohols catalyzed by aryl substituted N-hydroxyphthalimides.: Possible involvement of a charge-transfer complex
    Annunziatini, C
    Gerini, MF
    Lanzalunga, O
    Lucarini, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (10) : 3431 - 3438
  • [5] Argyropoulos D. S., 1997, BIOTECHNOLOGY PULP P, P127
  • [6] DRAMATIC SOLVENT EFFECTS ON THE ABSOLUTE RATE CONSTANTS FOR ABSTRACTION OF THE HYDROXYLIC HYDROGEN-ATOM FROM TERT-BUTYL HYDROPEROXIDE AND PHENOL BY THE CUMYLOXYL RADICAL - THE ROLE OF HYDROGEN-BONDING
    AVILA, DV
    INGOLD, KU
    LUSZTYK, J
    GREEN, WH
    PROCOPIO, DR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (10) : 2929 - 2930
  • [7] SUBSTITUENT EFFECTS ON THE STABILITIES OF PHENOXYL RADICALS AND THE ACIDITIES OF PHENOXYL RADICAL CATIONS
    BORDWELL, FG
    CHENG, JP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (05) : 1736 - 1743
  • [8] Determination of the substituent effect on the O-H bond dissociation enthalpies of phenolic antioxidants by the EPR radical equilibration technique
    Brigati, G
    Lucarini, M
    Mugnaini, V
    Pedulli, GF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) : 4828 - 4832
  • [9] A new selective free radical synthesis of aromatic aldehydes by aerobic oxidation of tertiary benzylamines catalysed by N-hydroxyimides and Co(II) under mild conditions.: Polar and enthalpic effects
    Cecchetto, A
    Minisci, F
    Recupero, F
    Fontana, F
    Pedulli, GF
    [J]. TETRAHEDRON LETTERS, 2002, 43 (19) : 3605 - 3607
  • [10] DACUNZO F, 2003, ORG BIOMOL CHEM, V1, P191