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化学学报
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化学学报 ›› 1991, Vol. 49 ›› Issue (6): 615-620. 上一篇    下一篇

研究论文

芳香族硝基化合物与苯硫酚钠盐的亲核取代反应: 自由基IPSO取代机理

刘有成;赵文轶   

  1. 兰州大学应用有机化学国家重点实验室
  • 发布日期:1991-06-15

Studies on the reaction of aromatic nitro compounds with sodium phenylthiolate radical IPSO substitution mechanism

LIU YOUCHENG;ZHAO WENYI   

  • Published:1991-06-15

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546

被引次数

1

作者通过苯硫酚钠盐与对硝基苯甲酸甲酯(1), 对硝基苯甲酸苯酯(2), 间硝基苯甲酸甲酯(3), 3,5-二硝基苯甲酸甲酯(4)和对二硝基苯(5)反应研究, 用自旋捕获技术检测到苯硫基自由基; 同时, 从产物混合物中分离到二苯基二硫化物PhSSPh。提出苯硫基自由基与芳香族硝基化合物1,2,3,4和5反应的自由基IPSO亲核取代机理。

关键词: 钠化合物, 酯, 电子自旋共振谱法, 取代反应, 苯 P, 苯硫酚 P, 苯甲酸 P, ＤＭＳＯ, 硝基苯, 二硫化物

Aromatic nitro compounds I (R = 4-CO2Me, 4-CO2Ph, 3-NO2-4-CO2Me) reacted with sodium phenylthiolate giving radical IPSO substitution products and di-Ph disulfide. The reaction mixtures were ESR active and the ESR spectra were consistent with those for the radical anions of I, resp. Using tertiary nitrosobutane as the spin trapping agent, the ESR spectrum for nitroxide tert-BuN(O) SPh was obtained. A radical IPSO substitution mechanism is proposed.

Key words: SODIUM COMPOUNDS, ESTERS, ELECTRON SPIN RESONANCE SPECTROMETRY, SUBSTITUTION REACTION, BENZENE P, BENZENETHIOL P, BENZENECARBOXYLIC ACID P, DMSO, NITROBENZENE, DISULFIDE

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