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SYNTHETIC COMMUNICATIONS · 2022 · IF 1.937

Di-tert-butyl peroxide (DTBP)-mediated synthesis of symmetrical N,N′-disubstituted urea/thiourea motifs from isothiocyanates in water

Jinchen Yang,Ling Chen,Yibo Dong,Jinli Zhang,Yangjie Wu

ABATRACTA direct approach to N,N′-disubstituted urea/thiourea from the self-condensation reactions of isothiocyanates in water has been developed. This access tolerated a wide range of functional groups on the aromatic ring, providing a practical and environment-friendly process to N,N′-disubstituted urea/thiourea in moderate to excellent yields from safe and easily available starting materials. A plausible mechanism of the desulfurization self-condensation reaction for urea was also proposed and the role of di-tert-butyl peroxide (DTBP) and copper catalyst in the present strategy was demonstrated with the help of ESI mass spectrometry of intermediate studies.

研究领域: 有机化学 · 绿色化学

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CHINESE JOURNAL OF CHEMICAL ENGINEERING · 2017 ·Vol. 25 ·期 10 ·1435-1441 · IF 1.174

Kinetics of water–isocyanate reaction in N,N-dimethylformamide

Zhirong Chen,Weitao Yang,Hong Yin,Shenfeng Yuan

The uncatalyzed reaction of p -tolyl isocyanate ( p -TI) with water in N , N -dimethylformamide (DMF) was investigated by high performance liquid chromatography (HPLC). The reactions were carried out at different temperatures from 293 K to 323 K, using various molar ratios of water to p -TI. DMF, as a special amide , was proved to be an efficient catalyst for water–isocyanate reaction. Under the reaction conditions in this study, substituted urea was the only final product observed. An appreciable amount of intermediate p -toluidine was detected. Concentrations of the isocyanate group as well as the amine and urea were determined as a function of time. New kinetic equations were deduced for each of the substance on the basis of a multistep mechanism, instead of a simple second order reaction as usual. Kinetic constants were calculated using the software MATLAB . Furthermore, the effects of temperature and concentrations of reactants on the reaction rate and amine content were discussed. The activation energy of each step was also determined.

研究领域: 物理化学 · 有机化学 · 反应动力学 · 高分子化学 · 催化化学 · 分析化学

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Di-tert-butyl peroxide (DTBP)-mediated synthesis of symmetrical N,N′-disubstituted urea/thiourea motifs from isothiocyanates in water

Kinetics of water–isocyanate reaction in N,N-dimethylformamide