Synthesis and characterization of trans-di(nitrobenzo)- and di(aminobenzo)-18-crown-6 derivatives with high selectivity

ABSTRACT

The dibenzo-18-crown-6 derivatives such as di(nitrobenzo)-18-crown-6 and di(aminobenzo)-18-crown-6 were synthesized by nitration reaction and catalytic hydrogenation with high selectivity. The chemical structures were determined by FTIR, ¹H NMR, ¹³C NMR, and UV. Regarding the mixture of Ac₂O and HNO₃ as nitrating agent, the reaction exhibited commendable trans-isomer selectivity. Effects of nitrating agent ratio, reaction temperature and reaction time on yield of trans-di(nitrobenzo)-18-crown-6 were investigated. The yield of trans-di(nitrobenzo)-18-crown-6 was 62.9% for nitrating agent ratio of 1/1, reaction temperature of 50 °C and reaction time of 5 h. Moreover, effect of reaction time on trans-di(aminobenzo)-18-crown-6 was also studied.

GRAPHICAL ABSTRACT

KEYWORDS:

• Catalytic hydrogenation
• high selectivity
• nitration reaction
• trans-di(aminobenzo)-18-crown-6
• trans-di(nitrobenzo)-18-crown-6

Additional information

Funding

This work is supported by the National Key R&D Program of China (2017YFB0603402), the National Natural Science Foundation of China (21576217), and the Fundamental Research Funds for the Central Universities (xjj2016044).