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化学学报
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化学学报 ›› 2011, Vol. 69 ›› Issue (20): 2407-2412. 上一篇    下一篇

研究论文

N-(ω-三丁基锡聚乙氧基醚)邻苯二甲酰亚胺的光诱导单电子转移成环反应

金英学1，苑望1，曲凤玉1，尹雄灿2，魏树权1，岳群峰1，谭广慧*,1   

  1. (1哈尔滨师范大学化学化工学院 哈尔滨 150025)
    (2釜山大学理学院化学系 釜山 609-735)
  • 投稿日期:2010-11-18 修回日期:2011-05-28 发布日期:2011-06-21
  • 通讯作者: 金英学 E-mail:yenghak@hrbnu.edu.cn
  • 基金资助:

    多供电子体-酰亚胺体系电子转移反应效率及大环化合物的合成与荧光感应性能研究

Photoinduced Single Electron Transfer Cyclization Reactions of N-(ω-Tributylstannylpolyethoxyether)phthalimides

Jin Yingxue1 Yuan Wang1 Qu Fengyu1 Ung Chan Yoon2 Wei Shuquan1 Yue Qunfeng1 Tan Guanghui*,1   

  1. (1 College of Chemistry & Engineering, Harbin Normal University, Harbin 150025)
    (2 Department of Chemistry, College of Natural Sciences, Pusan National University, Pusan, 609-735, Korea)
  • Received:2010-11-18 Revised:2011-05-28 Published:2011-06-21

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研究了N-(ω-三丁基锡聚乙氧基醚)邻苯二甲酰亚胺在甲醇溶剂中的光反应, 并与文献报道的N-(ω-三甲基硅聚乙氧基醚)邻苯二甲酰亚胺在甲醇中的光反应结果进行了比较. 发现光诱导单电子转移-脱三丁基锡成环反应过程比光诱导单电子转移-脱三甲基硅成环反应过程效率更高, 表明提高离去基团的离去能力可以提高单电子转移成环反应的选择性和环化物的产率. 所有新化合物和最终环化物的结构均经1H NMR, 13C NMR, HRMS验证.

关键词: 光诱导单电子转移, 三丁基锡, 三甲基硅, 离去基团, 环化物

The present study investigated the photoreaction of N-(ω-tributylstannylpolyethoxyether)- phthalimides in methanol solution. The results obtained were compared with that reported in previous studies. It is shown that photoinduced single electron transfer cyclization reaction proceeds by destannation at a higher efficiency than the cyclization reaction by desilylation, which suggests a feasibility of increasing the selectivity and productivity of single-electron cyclization reaction through improving the cleavability of the leaving group. The structure of all the new compounds and final cyclic compounds were characterized by using 1H NMR,13C NMR, HRMS technology.

Key words: photoinduced single electron transfer, tributylstannyl, trimethylsilyl, leaving group, cyclocompound