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



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   

  1. 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
  • 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 Haixiaa, Liu Yana, Hu Beib, Zhao Mengmengb, Ren Kaib, Xie Xiaominb, Xu Haoa, Zhang Zhaoguob   

  1. 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).

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