Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (1): 220-222.DOI: 10.6023/cjoc201307053 Previous Articles     Next Articles

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碘化钾在1,2-双(二溴甲基)苯及4位取代衍生物与反丁烯二腈反应中的作用

陈丽媛, 陈晓健, 张琦松, 沈永嘉   

  1. 结构可控先进功能材料及其制备教育部重点实验室 华东理工大学精细化工研究所 上海 200237
  • 收稿日期:2013-07-31 修回日期:2013-09-02 发布日期:2013-09-17
  • 通讯作者: 沈永嘉 E-mail:yjshen@ecust.edu.cn

Function of Potassium Iodide in the Reaction of 1,2-Bis-(dibromomethyl)benzene and Its 4-Substituted Derivatives with Fumaronitrile

Chen Liyuan, Chen Xiaojian, Zhang Qisong, Shen Yongjia   

  1. Laboratory of Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237
  • Received:2013-07-31 Revised:2013-09-02 Published:2013-09-17
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21076078).

1,2-Bis(dibromomethyl)benzene and its 4-substituted derivatives would not react with fumaronitrile in N,N-dimethylformamide in the absence of potassium iodide. However, the same reaction happened in the presence of potassium iodide. The major product was 2,3-dicyanonaphthalene or its corresponding substituted derivatives. The yields depended on the adding amounts of the potassium iodide. When the adding amount of potassium iodide was equal to the molar amount of bromine atoms in 1,2-bis(dibromomethyl)benzene or its 4-substituted derivatives, the reaction was substantially completed and the main product was 2,3-dicyanonaphthalene or its corresponding substituted derivatives with yield of 87.1%. Based on this fact, the function of potassium iodide was not a catalyst but a reaction reagent, and the reaction mechanism was proposed.

Key words: potassium iodide, 1,2-bis(dibromomethyl)benzene, fumaronitrile, mechanism