Photoinduced Single Electron Transfer Cyclization Reactions of N-(Trimethylstannyl terminated substituent group)imide

doi:10.6023/cjoc201205027

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (12): 2363-2367.DOI: 10.6023/cjoc201205027 Previous Articles Next Articles

Notes

N-(末端三丁基锡取代基)酰亚胺的光诱导单电子转移成环反应

金英学, 王欣, 曲凤玉, 谭广慧, 岳群峰

哈尔滨师范大学化学化工学院哈尔滨 150025

收稿日期:2012-05-22 修回日期:2012-08-10 发布日期:2012-08-21
通讯作者: 岳群峰 E-mail:yenghak@hrbnu.edu.cn
基金资助:
国家自然科学基金(Nos. 20972036, 21171045)、黑龙江省自然科学基金(No. B200913)和黑龙江省高校科技创新团队建设计划(No. 2011TD010)资助项目.

Photoinduced Single Electron Transfer Cyclization Reactions of N-(Trimethylstannyl terminated substituent group)imide

Jin Yingxue, Wang Xin, Qu Fengyu, Tan Guanghui, Yue Qunfeng

College of Chemistry & Engineering, Harbin Nomal University, Harbin 150025

Received:2012-05-22 Revised:2012-08-10 Published:2012-08-21
Supported by:
Project supported by the National Natural Sciences Foundation of China (Nos. 20972036, 21171045), the Natural Sciences Foundation of Heilongjiang Province (No. B200913) and the Program for Scientific Technological Innovation Team Construction in Universites of Heilongjiang Province (No. 211TD010).

Two novel intramolecularly electronical donor-acceptor systemes N-[2-(2-tributylstannylmethyl-sulfenyl)-ethyl]phthalimide (1a) and N-(3-tributylstanylpropyl)maleimide (1b), were synthesized, and their photoinduced single electron transfer (SET) reactions in MeOH, CH₃CN-30% H₂O and pure CH₃CN were carried out, respectively. Compound 1a occurred intramolecular SET to provide cyclic amidol 2 with highly yield and high regioselectivity. Compound 1b occurred intramolecular single electron transfer (SET) to provide cyclic amidol 3 with small amount of photoinduced [2+2] dimerization product 4. Structures of all new compounds were characterized by MS (FAB) and NMR data.

Key words: photoinduced, single electron transfer (SET), cyclic reaction, tributyistannyl, imide

Cite this article

Jin Yingxue, Wang Xin, Qu Fengyu, Tan Guanghui, Yue Qunfeng. Photoinduced Single Electron Transfer Cyclization Reactions of N-(Trimethylstannyl terminated substituent group)imide[J]. Chin. J. Org. Chem., 2012, 32(12): 2363-2367.

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N-(末端三丁基锡取代基)酰亚胺的光诱导单电子转移成环反应

Photoinduced Single Electron Transfer Cyclization Reactions of N-(Trimethylstannyl terminated substituent group)imide

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