Aminolysis of 4-nitrophenyl phenyl carbonate and thionocarbonate: effects of amine nature and modification of electrophilic center from C[double bond]O to C[double bond]S on reactivity and mechanism.

@article{Um2008AminolysisO4,
  title={Aminolysis of 4-nitrophenyl phenyl carbonate and thionocarbonate: effects of amine nature and modification of electrophilic center from C[double bond]O to C[double bond]S on reactivity and mechanism.},
  author={I. Um and Sora Yoon and Hye-Ran Park and Hyun-Joo Han},
  journal={Organic & biomolecular chemistry},
  year={2008},
  volume={6 9},
  pages={
          1618-24
        }
}
  • I. Um, Sora Yoon, +1 author Hyun-Joo Han
  • Published 2008
  • Chemistry, Medicine
  • Organic & biomolecular chemistry
    • A kinetic study is reported for the reactions of 4-nitrophenyl phenyl carbonate (5) and thionocarbonate (6) with a series of alicyclic secondary amines in 80 mol% H(2)O-20 mol% DMSO at 25.0 +/- 0.1 degrees C. The plots of k(obsd) vs. amine concentration are linear for the reactions of 5. On the contrary, the plots for the corresponding reactions of 6 curve upward as a function of increasing amine concentration, indicating that the reactions proceed through two intermediates (i.e., a… CONTINUE READING
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    References

    SHOWING 1-10 OF 82 REFERENCES
    Aminolyses of 4-nitrophenyl phenyl carbonate and thionocarbonate: effect of modification of electrophilic center from C=O to C=S on reactivity and mechanism.
    • 55
    Effect of amine nature on reaction mechanism: aminolyses of o-4-nitrophenyl thionobenzoate with primary and secondary amines.
    • 63
    Kinetics and mechanisms of the reactions of 4-nitro- and 3-nitrophenyl 4-methylphenyl thionocarbonates with alicyclic amines and pyridines
    • 25
    • PDF
    Kinetic study of the aminolysis and pyridinolysis of O-phenyl and O-ethyl O-(2,4-dinitrophenyl) thiocarbonates. A remarkable leaving group effect.
    • 33
    Kinetics and mechanism of the aminolysis of O-aryl S-methyl thiocarbonates.
    • 41
    Aminolysis of Y-substituted phenyl diphenylphosphinates and benzoates: effect of modification of electrophilic center from C=O to P=O.
    • 75
    • PDF
    Effects of amine nature and nonleaving group substituents on rate and mechanism in aminolyses of 2,4-dinitrophenyl X-substituted benzoates.
    • 99
    • PDF
    Aminolysis of 2,4-dinitrophenyl X-substituted benzoates and Y-substituted phenyl benzoates in MeCN: effect of the reaction medium on rate and mechanism.
    • 72
    Kinetics and mechanism of the anilinolysis of aryl 4-nitrophenyl carbonates in aqueous ethanol.
    • 52
    • PDF
    Kinetics and mechanism of the reactions of S‐4‐nitrophenyl 4‐methylthiobenzoate with secondary alicyclic amines and pyridines
    • 11
    • PDF