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

Dongyun Wu; Chunhai Yi; Beibei Zhang; Bolun Yang

doi:10.1080/00397911.2017.1402350

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

Dongyun Wu
, Chunhai Yi
, Beibei Zhang
, Bolun Yang

化学工程与技术学院

Xi'an Jiaotong University

科研成果: 期刊稿件 › 文章 › 同行评审

10 引用（Scopus）

摘要

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.

源语言	英语
页（从-至）	329-335
页数	7
期刊	Synthetic Communications
卷	48
期	3
DOI	https://doi.org/10.1080/00397911.2017.1402350
出版状态	已出版 - 1 2月 2018

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title = "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.",

keywords = "Catalytic hydrogenation, high selectivity, nitration reaction, trans-di(aminobenzo)-18-crown-6, trans-di(nitrobenzo)-18-crown-6",

author = "Dongyun Wu and Chunhai Yi and Beibei Zhang and Bolun Yang",

note = "Publisher Copyright: {\textcopyright} 2017 Taylor \& Francis.",

year = "2018",

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doi = "10.1080/00397911.2017.1402350",

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TY - JOUR

T1 - Synthesis and characterization of trans-di(nitrobenzo)- and di(aminobenzo)-18-crown-6 derivatives with high selectivity

AU - Wu, Dongyun

AU - Yi, Chunhai

AU - Zhang, Beibei

AU - Yang, Bolun

PY - 2018/2/1

Y1 - 2018/2/1

N2 - 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.

AB - 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.

KW - Catalytic hydrogenation

KW - high selectivity

KW - nitration reaction

KW - trans-di(aminobenzo)-18-crown-6

KW - trans-di(nitrobenzo)-18-crown-6

UR - https://www.scopus.com/pages/publications/85041339354

U2 - 10.1080/00397911.2017.1402350

DO - 10.1080/00397911.2017.1402350

M3 - 文章

AN - SCOPUS:85041339354

SN - 0039-7911

VL - 48

SP - 329

EP - 335

JO - Synthetic Communications

JF - Synthetic Communications

IS - 3

ER -

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

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