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由ET反应制备5(6)—羟基—2—烷基—1,4—二甲氧基苯
引用本文:赵宇,李薇,赵成学,陈庆云.由ET反应制备5(6)—羟基—2—烷基—1,4—二甲氧基苯[J].上海交通大学学报,2001,35(4):591-594.
作者姓名:赵宇  李薇  赵成学  陈庆云
作者单位:1. 上海交通大学化学化工学院,
2. 中国科学院上海有机化学研究所,
基金项目:国家自然科学基金资助项目(29772022)
摘    要:通过单电子转移(ET)反应间接制备了5(6)-羧基-2-烷基-1,4-二甲氧基苯,通过2-烷基-1,4-二甲氧基苯(1)与过氧化二对硝基苯甲酰(2)的电子转移反应,在苯环上引入芳酰氧基;然后在温和条件下水解,可得到互为位置异构体的两种稀有酚3和4。用∧1HNMR、IR、MS分别表征了化合物的结构,反应机理研究发现,反应物2在1存在条件下,其分解速度急剧加快;用顺磁共振技术检测到了反应过程中产生的阳离子基信号,证明反应物1和2的反应是单电子转移反应,该反应条件温和,产率较高,产物易于分离纯化,是一种制备该类酚的简易方法。

关 键 词:  单电子转移  阳离子自由基  5(6)-羟基-2-烷基-1  4-二甲基苯  ET反应
文章编号:1006-2467(2001)04-0591-04
修稿时间:2000年8月30日

Preparation of 5(or 6)-Hydroxy-2-Alkyl-1, 4-Dimethoxybenzene via ET Reaction
ZHAO Yu,LI Wei,ZHAO Cheng-xue,CHEN Qing-yun.Preparation of 5(or 6)-Hydroxy-2-Alkyl-1, 4-Dimethoxybenzene via ET Reaction[J].Journal of Shanghai Jiaotong University,2001,35(4):591-594.
Authors:ZHAO Yu  LI Wei  ZHAO Cheng-xue  CHEN Qing-yun
Institution:ZHAO Yu 1,LI Wei 1,ZHAO Cheng xue 1,CHEN Qing yun 2
Abstract:A facile preparation of 5(or 6) Hydroxy 2 Alkyl 1,4 Dimethoxybenzene via one electron transfer was reported. In the reaction of 2 Alkyl 1,4 Dimethoxybenzene (1) and 4 nitrobenzoyl peroxide (2), the ring is substituted by 4 nitrobenzoyloxy group in C 5 or C 6 position, respectively. Then the products obtained were hydrolyzed. Two corresponding isomers of the substituted phenols were obtained and characterized by 1H NMR, MS and IR, respectively. This reaction was carried out in the mild condition with high yield and the products were subject to facile isolation. The great acceleration of decomposition of reactant 2 in the presence of 1 was observed by kinetic studies. The signal of radical cation was detected by Electron Spin Resonance technique. One electron transfer mechanism involving radical cation generation was proved in the reaction of donor 1 and accepter 2.
Keywords:phenol  one  electron transfer  radical cation
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