6566-25-2Relevant academic research and scientific papers
Kinetics of Hydrolysis of 1-Acetoxy-, 1-Acetoxy-8-hydroxy-, and 1,8-Diacetoxynaphthalenes; Intramolecular Participation by a Hydroxy Group
Hibbert, Frank,Spiers, Karen J.
, p. 571 - 574 (1988)
Consecutive hydrolysis of the acetoxy groups in 1,8-diacetoxynaphthalene in aqueous alkaline solution can be studied kinetically because hydrolysis occurs more rapidly for the diacetate than for 1-acetoxy-8-hydroxynaphthalene which is mostly present in the ionised form.The dependence of the rate coefficient (k2) for hydrolysis of 1-acetoxy-8-hydroxynaphthalene on the concentration of hydroxide ion is complex because of the equilibrium between the ionised and un-ionised forms and their different reactivities.The equilibrium between the ionised and un-ionised forms has been measured separately and the data are combined with the kinetic results to show that the linear dependence of k2 on -> at high concentrations is due to reaction of the ionised form with OH-.At low concentrations, the curved dependence of k2 on -> can be explained by reaction of ionised 1-acetoxy-8-hydroxynaphthalene with solvent.The value of the rate coefficient (k4) for this reaction, in comparison with the value for the reaction of 1-acetoxynaphthalene with water, shows that the hydroxy group assists the attack of water by intramolecular general base catalysis.A kinetic solvent isotope effect K4(H2O)/k4(D2O) 2.2 +/- 0.5 is observed.
Conversion of N-aromatic amides to O-aromatic esters
Glatzhofer, Daniel T.,Roy, Raymond R.,Cossey, Kimberly N.
, p. 2349 - 2352 (2007/10/03)
(Matrix Presented) N-Aromatic secondary amides can be transformed into O-aromatic esters in high yield via N-nitrosamide intermediates. The amides can be generated in situ from the corresponding aromatic amines or nitro compounds, and phenols can easily be made from the esters. The reaction can be modified by addition of methyl methacrylate or toluene at 0 °C to give polymerization or deamination, respectively. The rearrangement mechanism may involve radical formation and recombination.
