586-11-8Relevant articles and documents
A convenient synthesis of phenols
Kristianslund, Renate,Vik, Anders,Hansen, Trond V.
supporting information, p. 2809 - 2814 (2018/12/04)
Anilines are rapidly, often within 60 minutes, converted into the corresponding phenols in up to 87% isolated yield. The presented experimentally simple protocol display broad compatibility with a variety of functional groups, and in particular, well suited for the preparation of methyl-substituted phenols. Such phenols are not easily available by other synthetic approaches. The formation of phenolic radical coupling products was not observed even for activated anilines using this open flask method.
Kinetics and mechanism of base-catalysed degradations of substituted aryl-N-hydroxycarbamates, their N-methyl and N-phenyl analogues
Beier, Petr,Mindl, Jaromir,Sterba, Vojeslav,Hanusek, Jiri
, p. 562 - 569 (2007/10/03)
The kinetics and mechanism of the degradation reactions of substituted phenyl N-hydroxycarbamates and their N-methyl and N-phenyl analogues have been studied at pseudo-first-order reaction conditions in aqueous buffers and sodium hydroxide solutions at 20°C and 60°C and at I = 1 mol·1 -1. The dependence of log kobs on pH for phenyl N-hydroxycarbamates at pH 13 is linear with the unit slope; at pH 10-12 log kobs is pH independent. The Bronsted coefficient βlg is about -1 (pH 7-13) and -1.53 (pH > 13) indicating that the degradation reaction of phenyl N-hydroxycarbamates follows an ElcB mechanism giving the corresponding phenol/phenolate and HO-N=C=O. The latter species undergoes further decomposition to give carbonate, nitrogen and ammonia as final products. In contrast to the phenyl N-hydroxycarbamates the N-methyl derivatives at pH 7-9 undergo degradation to the corresponding phenol/phenolate, carbonate and methylamine via a concerted mechanism (βlg is about - 0.75). The only exception is 4-nitrophenyl N-hydroxy-N-methylcarbamate in which the predominant break down pathway proceeds via the Smiles rearrangement to give sodium N-methyl-(4-nitrophenoxy)carbamate. At pH > 9 the reaction of N-hydroxy-N-methylcarbamates is kinetically complex: the dependence of absorbance on time is not exponential and it proceeds as a consecutive two-step reaction. N-Hydroxy-N-phenylcarbamate under the same conditions undergoes degradation to phenol, carbonate, aniline and azoxybenzene.
Substitution for a nitro group in 1,3,5-trinitrobenzene and meta-substituted 1,3-dinitrobenzenes under the action of oximes
Shevelev, Svyatoslav A.,Vatsadze, Irina A.,Dutov, Mikhail D.
, p. 196 - 198 (2007/10/03)
The title reaction was performed with 1,3,5-trinitrobenzene and 1-X-3,5-dinitrobenzenes (X = CF3, ArO) in the presence of K2CO3in N-methylpyrrolidone or DMF solutions to form O-3,5-dinitrophenyl oximes or O-3-X-5-nitrophenyl oximes, respectively.
