由ET反应制备5(6)-羟基-2-烷基-1,4-二甲氧基苯  

Preparation of 5(or 6)-Hydroxy-2-Alkyl-1, 4-Dimethoxybenzene via ET Reaction

作　　者：赵宇[1] 李薇[1] 赵成学[1] 陈庆云[2] 

机构地区：[1]上海交通大学化学化工学院,上海200240 [2]中国科学院上海有机化学研究所,上海200032

出　　处：《上海交通大学学报》2001年第4期591-594,共4页Journal of Shanghai Jiaotong University

基　　金：国家自然科学基金资助项目! (2 9772 0 2 2 )

摘　　要：通过单电子转移 (ET)反应间接制备了 5(6) -羟基 - 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 1H NMR、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 。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.

关 键 词：酚 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 

分 类 号：O625.11[理学—有机化学]