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

doi:10.6023/cjoc201304042

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (9): 1950-1954.DOI: 10.6023/cjoc201304042 Previous Articles Next Articles

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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

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

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)

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 1～4 were characterized by MS, NMR data.

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

Cite this article

Liang Boying, Jin Yingxue, Yu Shasha, Qu Fengyu, Tan Guanghui. Synthesis of Thiacrown Ether and Nitrogen Crown Ether by Photoinduced Single Electron Transfer Reaction[J]. Chin. J. Org. Chem., 2013, 33(9): 1950-1954.

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光诱导单电子转移反应合成硫杂、氮杂冠醚

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

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