有机化学 ›› 2013, Vol. 33 ›› Issue (09): 1950-1954.DOI: 10.6023/cjoc201304042 上一篇    下一篇

研究论文

光诱导单电子转移反应合成硫杂、氮杂冠醚

粱波颖, 金英学, 于沙沙, 曲凤玉, 谭广慧   

  1. 哈尔滨师范大学化学化工学院化学系 哈尔滨 150025
  • 收稿日期:2013-04-25 修回日期:2013-05-28 发布日期:2013-06-09
  • 通讯作者: 金英学,谭广慧 E-mail:yenghak@hrbnu.edu.cn;tgh.123@163.com
  • 基金资助:

    国家自然科学基金(Nos. 20972036, 21272048);黑龙江省自然科学基金(No. B20913);黑龙江省高校科技创新团队建设计划(No. 2011TD010)资助项目

Synthesis of Thiacrown Ether and Nitrogen Crown Ether by Photoinduced Single Electron Transfer Reaction

Liang Boying, Jin Yingxue, Yu Shasha, Qu Fengyu, Tan Guanghui   

  1. College of Chemistry & Chemical Engineering, Harbin Normal University, Harbin 150025
  • Received:2013-04-25 Revised:2013-05-28 Published:2013-06-09
  • Supported by:

    Project supported by the National Natural Sciences Foundation of China (Nos. 20972036, 21272048), the Natural Sciences Foundatjion of Heilongjiang Province (No. B20913), and the Program for Scientific Technological Innovation Team Construction in Universities of Heilongjiang Province (No. 211TD010)

合成了以邻苯二甲酰亚胺为电子受体, 末端三甲基硅烷基醚链为电子给体的新的分子内给受电子体系N-(末端三甲基硅烷基硫杂醚链)邻苯二甲酰亚胺(1)和N-(末端三甲基硅烷基氮杂醚链)邻苯二甲酰亚胺(2). 化合物12在甲醇中进行光反应, 在光诱导下发生分子内单电子转移反应, 以很高的产率和很高的区域选择性生成硫杂冠醚(3)和氮杂冠醚(4). 化合物14的化学结构经核磁共振、质谱的验证.

关键词: 光反应, 单电子转移(SET), 硫杂冠醚, 氮杂冠醚, 区域选择性

Novel intramolecularly electronical donor-acceptor systems of N-(trimethylsilyl teminated enesulfenyl ether)phthalimide (1) and N-(trimethylsilyl teminated nitrogen ether)phthalimide (2) were synthesized. Compounds 1 and 2 were irradiated in methanol and the photoinduced intramolecular single electron transfer provided thiacrown ether (3) and nitrogen crown ether (4) with high yield and high regioselectivity. Structures of compounds 14 were characterized by MS, NMR data.

Key words: photoreaction, single electron transfer (SET), thiacrown ether, nitrogen crown ether, regioselectivity