Synthesis of Exo-norborn-5-ene-2,3-anhydride via Isomerization

doi:10.6023/cjoc201503018

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (8): 1759-1764.DOI: 10.6023/cjoc201503018 Previous Articles Next Articles

NOTE

异构化合成顺-5-降冰片烯-外-2,3-二酸酐的研究

陈海霞^a, 刘艳^a, 胡北^b, 赵梦梦^b, 任凯^b, 谢小敏^b, 徐浩^a, 张兆国^b

a 南京工业大学理学院南京 211816;
b 上海交通大学化学化工学院上海 200240

收稿日期:2015-03-13 修回日期:2015-04-29 发布日期:2015-04-30
通讯作者: 张兆国 E-mail:zhaoguo@sjtu.edu.cn
基金资助:
国家自然科学基金(No. 21272156)资助项目.

Synthesis of Exo-norborn-5-ene-2,3-anhydride via Isomerization

Chen Haixia^a, Liu Yan^a, Hu Bei^b, Zhao Mengmeng^b, Ren Kai^b, Xie Xiaomin^b, Xu Hao^a, Zhang Zhaoguo^b

a College of Sciences, Nanjing Tech University, Nanjing 211816;
b School of Chemistry and Chemical Engineering, Shanghai Jiaotong University, Shanghai 200240

Received:2015-03-13 Revised:2015-04-29 Published:2015-04-30
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21272156).

1. Synthesis of Exo-norborn-5-ene-2,3-anhydride via Isomerization.PDF(1688KB)

Abstract

High purity exo-norborn-5-ene-2,3-anhydride was synthesized by Diels-Alder reaction of freshly distilled cyclopentadiene and maleic anhydride, isomerization and recrystallization. Acid-promoted isomerization, base-promoted isomerization and thermal isomerization of endo-norborn-5-ene-2,3-anhydride were studied in detail. 1,2-Dimethoxybenzene was found to be a competent solvent in the thermal isomerization of endo-norborn-5-ene-2,3-anhy-dride, and reaction time and concentration of substrate were also optimized. Furthermore, an effective protocol was developed to obtain exo-norborn-5-ene-2,3-anhydride with high purity in a overall yield of 66.5%.

Key words: exo-norborn-5-ene-2,3-anhydride, Diels-Alder reaction, isomerization, 1,2-dimethoxybenzene

Cite this article

Chen Haixia, Liu Yan, Hu Bei, Zhao Mengmeng, Ren Kai, Xie Xiaomin, Xu Hao, Zhang Zhaoguo. Synthesis of Exo-norborn-5-ene-2,3-anhydride via Isomerization[J]. Chin. J. Org. Chem., 2015, 35(8): 1759-1764.

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异构化合成顺-5-降冰片烯-外-2,3-二酸酐的研究

Synthesis of Exo-norborn-5-ene-2,3-anhydride via Isomerization

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