E-Z Isomerization of 1, 5-Bromotrichloromethylation Reaction Products and Trisubstituted Styrenes

doi:10.6023/cjoc201712002

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (6): 1507-1515.DOI: 10.6023/cjoc201712002 Previous Articles Next Articles

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1,5-溴三氯甲基化产物及三取代苯乙烯的E-Z异构化

李进, 陈靖之, 黄文浩, 程旭

南京大学化学化工学院南京 210023

收稿日期:2017-12-02 修回日期:2018-01-30 发布日期:2018-02-06
通讯作者: 程旭,E-mail:chengxu@nju.edu.cn E-mail:chengxu@nju.edu.cn
基金资助:
国家自然科学基金（No.21572099，21332005）资助项目.

E-Z Isomerization of 1, 5-Bromotrichloromethylation Reaction Products and Trisubstituted Styrenes

Li Jin, Chen Jingzhi, Huang Wenhao, Cheng Xu

School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023

Received:2017-12-02 Revised:2018-01-30 Published:2018-02-06
Contact: 10.6023/cjoc201712002 E-mail:chengxu@nju.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21572099, 21332005).

1. E-Z Isomerization of 1, 5-Bromotrichloromethylation Reaction Products and Trisubstituted Styrenes.PDF(5871KB)

Abstract

1,5-Bromotrichloromethylation of α-cyclopropylstyrenes via a radical chain pathway was achieved with Ir[dF(CF₃)ppy]₂(dtbbpy)PF₆ as a photoinitiator under visible-light irradiation to give trisubstituted styrenes with Z/E ratio of 30:70. When the reaction mixture was further irradiated, the Z/E ratio could be reversed and increased to 99:1, probably via an energy-transfer pathway involving the Ir photocatalyst. This visible-light-induced catalytic isomerization protocol could also be applied to trisubstituted styrenes to obtain products with Z/E ratios up to 99:1.

Key words: photochemistry, radical, alkene, isomerization

Cite this article

Li Jin, Chen Jingzhi, Huang Wenhao, Cheng Xu. E-Z Isomerization of 1, 5-Bromotrichloromethylation Reaction Products and Trisubstituted Styrenes[J]. Chin. J. Org. Chem., 2018, 38(6): 1507-1515.

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1,5-溴三氯甲基化产物及三取代苯乙烯的E-Z异构化

E-Z Isomerization of 1, 5-Bromotrichloromethylation Reaction Products and Trisubstituted Styrenes

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