Chinese Journal of Organic Chemistry >
Function of Potassium Iodide in the Reaction of 1,2-Bis-(dibromomethyl)benzene and Its 4-Substituted Derivatives with Fumaronitrile
Received date: 2013-07-31
Revised date: 2013-09-02
Online 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
Chen Liyuan , Chen Xiaojian , Zhang Qisong , Shen Yongjia . Function of Potassium Iodide in the Reaction of 1,2-Bis-(dibromomethyl)benzene and Its 4-Substituted Derivatives with Fumaronitrile[J]. Chinese Journal of Organic Chemistry, 2014 , 34(1) : 220 -222 . DOI: 10.6023/cjoc201307053
[1] Rong, G.-B. Fundamentals of University Organic Chemistry, 2nd ed., East China University of Science and Technology Press, Shanghai, 2006, p. 268 (in Chinese).
(荣国斌, 大学有机化学基础(第二版), 华东理工大学出版社, 上海, 2006, p. 268.)
[2] Duan, W.-B.; Sheng, Y.-H.; Wu, Y.-Q.; Zuo, X.; Yang, S.-L.; Chen, N.-S. J. Nat. Sci. Heilongjiang Univ. 1997, 14(3), 105 (in Chinese).
(段武彪, 生会云, 吴谊群, 左霞, 杨素苓, 陈耐生, 黑龙江大学自然科学学报, 1997, 14(3), 105.)
[3] Whrle, D.; Shopova, M.; Müller, S.; Milev, A. D.; Mantareva, V. N.; Krastev, K. K. J. Photochem. Photobiol. B: Biol. 1993, 21, 155.
[4] Niu, X.-Y.; Wu, Y.-Q.; Chen, N.-S. J. Nat. Sci. Heilongjiang Univ. 2004, 21(3), 116 (in Chinese).
(牛晓宇, 吴谊群, 陈耐生, 黑龙江大学自然科学学报, 2004, 21(3), 116.)
[5] Plater, M. J.; Jeremiah, A.; Bourhill, G. J. Chem. Soc., Perkin Trans. 1 2002, 91.
[6] Wang, X..-B.; Tang, D.-H.; Wang, F.-Q.; Zhen, Z.; Zhang, J.-C.; Liu, X.-H. Chin. J. Org. Chem. 1999, 19, 249 (in Chinese).
(王小兵, 唐代华, 王凤奇, 甄珍, 张建成, 刘新厚, 有机化学, 1999, 19, 249.)
[7] Iqbal, Z.; Lyubimtsev, A.; Hanack, M.; Ziegler, T. Tetrahedron Lett. 2009, 50, 5681.
[8] Polley, R.; Hanack, M. J. Org. Chem. 1995, 60, 8278.
[9] Casay, G. A.; Narayanan, N.; Evans, L.; Czuppon, T.; Patonay, G. Talanta 1996, 43, 1997.
[10] Brasseur, N.; Nguyen, T. L.; Langlois, R.; Ouellet, R.; Marengo, S.; Houde, D.; Lier, J. E. J. Med. Chem. 1994, 37, 415.
[11] Luo, Y.-R. Handbook of Bond Dissociation Energies in Organic Compounds, Science Press, Beijing, 2005, p.129 (in Chinese).
(罗渝然, 化学键能数据手册, 科学出版社, 北京, 2005, p. 129)
/
| 〈 |
|
〉 |
