Cuprous Chloride Catalyzed Isomerization of 3-Chloro-1-butene to Crotyl Chloride

doi:10.6023/cjoc1109212

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (04): 794-798.DOI: 10.6023/cjoc1109212 Previous Articles Next Articles

Notes

氯化亚铜催化3-氯-1-丁烯异构为1-氯-2-丁烯研究

董建勋^a, 阎智峰^b, 石玉坤^a, 胡晓静^a, 丁真贞^a, 赵伟玲^a, 宋娟娟^a, 黄唯平^a

a 南开大学化学系天津 300071;
b 河南省伟华安全科技有限公司郑州 450000

收稿日期:2011-09-21 修回日期:2011-11-12 发布日期:2012-04-24
通讯作者: 黄唯平 E-mail:huangw@eyou.com
基金资助:
国家自然科学基金(No. 21071086)资助项目.

Cuprous Chloride Catalyzed Isomerization of 3-Chloro-1-butene to Crotyl Chloride

Dong Jianxun^a, Yan Zhifeng^b, Shi Yukun^a, Hu Xiaojing^a, Ding Zhenzhen^a, Zhao Weiling^a, Song Juanjuan^a, Huang Weiping^a

a College of Chemistry, Nankai University, Tianjin 300071;
b Henan Weihua Safety Assessment Company Limited, Zhengzhou 450000

Received:2011-09-21 Revised:2011-11-12 Published:2012-04-24
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21071086).

1. Cuprous Chloride Catalyzed Isomerization of 3-Chloro-1-butene to Crotyl Chloride.PDF(3279KB)

Abstract

The isomerization of 3-chloro-1-butene to crotyl chloride was carried out in the homogeneous catalytic system containing cuprous salt and dimethylformamide. Factors such as solvent, temperature, and content of catalyst that influence the reaction were investigated. The type of solvent and content of catalyst had great effect on the isomerization. Equilibrium constant of the title reaction reached 3.88, which was kept for 5 h at 60 ℃ under the optimal condition. The process of isomerization was monitored with in-situ FTIR-ATR and the possible reaction mechanism was suggested in this paper.

Key words: 3-chloro-1-butene, crotyl chloride, cuprous chloride, isomerization

Cite this article

Dong Jianxun, Yan Zhifeng, Shi Yukun, Hu Xiaojing, Ding Zhenzhen, Zhao Weiling, Song Juanjuan, Huang Weiping. Cuprous Chloride Catalyzed Isomerization of 3-Chloro-1-butene to Crotyl Chloride[J]. Chin. J. Org. Chem., 2012, 32(04): 794-798.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Xu, K.-X. Handbook of Organic Chemical Materials and Intermediates, Liaoning Petrochemical Engineering Technical Information Master Station, Shenyang, 1989, p. 60 (in Chinese). (徐克勋, 有机化工原料及中间体便览, 辽宁省石油化工技术情报总站, 沈阳, 1989, p. 60.)

[2] Kharasch, M. S.; Margolis, E. T.; Mayo, F. R. J. Org. Chem. 1936, 1, 393.

[3] Mascavage, L. M.; Dalton, D. R. Tetrahedron Lett. 1991, 32, 3461.

[4] DeWolfe, R. H.; Young, W. G. Chem. Rev. 1956, 56, 753.

[5] Hemmingson, J. A. J. Chem. Soc. B 1971, 1347.

[6] Dittmer, D. C.; Marcantonio, A. F. J. Org. Chem. 1964, 29, 3473.

[7] Winstein, S.; Young, W. G. J. Am. Chem. Soc. 1936, 58, 104.

[8] Kharasch, M. S.; Kritchevsky, J.; Mayo, F. R. J. Org. Chem. 1937, 2, 489.

[9] Lane, J. F.; Fentress, J.; Sherwood Jr, L. T. J. Am. Chem. Soc. 1944, 66, 545.

[10] Yang, L.; Houser, R. P. Inorg. Chem. 2006, 45, 9416.

[11] Chadha, S.; Nelson, W. H.; Emrich, R.; Lindesmith, E. Appl. Spectrosc. 1993, 47, 475.

[12] Lu, M.; Wang, S.-W.; Li, J. J. Nanjing Univ. Sci. Technol. 2007, 31, 533 (in Chinese). (陆明, 汪水旺, 李剑, 南京理工大学学报, 2007, 31, 533.)

[13] Braude, E. A. Quart. Rev. 1950, 4, 419.

[14] Young, W. G.; Winstein, S.; Goering, H. L. J. Am. Chem. Soc. 1951, 73, 1958.

[15] Puentes, E.; Mamalis, I.; Noels, A. F. J. Catal. 1983, 82, 365.

[16] Mamalis, I.; Grandjean, J.; Noels, A. F. Catal. Today 1987, 1, 59.

[17] Cristol, S. J.; Lee, G. A. J. Am. Chem. Soc. 1969, 91, 7554.

[18] Schei, S. H.; Klaeboe, P. Acta Chem. Scand. A 1983, 37, 315.

[19] Schei, S. H. J. Mol. Struct. 1984, 118, 319.

[20] Crowder, G. A.; Smyrl, N. J. Mol. Struct. 1971, 10, 373.

[21] Klemperer, W.; Rice, S. A.; Berry, R. S. J. Am. Chem. Soc. 1957, 79, 1810.

氯化亚铜催化3-氯-1-丁烯异构为1-氯-2-丁烯研究

Cuprous Chloride Catalyzed Isomerization of 3-Chloro-1-butene to Crotyl Chloride

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Hong-Chao Chen, Yichen Wu, Yang Yu, Peng Wang. Pd-Catalyzed Isomerization of Alkenes [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 742-757.
[2]	Wei Ding, Bowen Cheng, Meng Wang, Qingyu Dou, Siying Li, Peng Zhang, Qianfu Luo. Advances in Aggregation-Induced Emission Molecules Based on Organic Photochromism [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 363-383.
[3]	Shijie Li, Qiuyue Nie, Zhenyu Ji, Huiming Hua, Gongli Tang. Combinatorial Biosynthesis Mediates the Discovery of Novel Tetracyclines with Isomerized C-4 Hydroxyl [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3297-3302.
[4]	Huang Jing, Yang Yihua, Feng Juan, Li Junzhang, Liu Shouxin. Research Progress on cis-/trans-Isomerization of Cyclic Peptide [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1473-1483.
[5]	Zhang Shuo, Lou Jianfang, Wang Jiarui, Song Zihe, Peng Dan, Wang Feng, Yan Zhiwang, Cui Shiqi, Liu Yifan, Mu Qiuhong, Li Jinhui. Zn/Y Bimetallic Relay Catalysis: One Pot Intramolecular Cyclo-isomerization/Intermolecular Alder-Ene Reaction toward Oxazole α-Hydroxy Amide Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 704-713.
[6]	Zhang Qi-Qi, Lin Peng-Peng, Yang Ling, Tan Dong-Hang, Feng Si-Xin, Wang Honggen, Li Qingjiang. Visible-Light-Promoted Ir(III)-Catalyzed Z→E Isomerization of Monofluorostilbenes [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3314-3326.
[7]	Yan Jianfeng, Zhang Ruiqi, Yuan Ye, Yuan Yaofeng. 4,4'-Dimethoxy-triphenylamine Conjugated Azobenzene Photochromic Switches:Synthesis, Electrochemical and Photoisomerization Studies [J]. Chin. J. Org. Chem., 2019, 39(7): 2009-2017.
[8]	Xu Jiao, Zhang Lihong, Zhang Meiqi, Liu Xiubo, Ma Wei, Tang Yixin, Wang Daolin. Iodine-Dimethyl sulfoxide Promoted Synthesis of Novel TetracyclicThiazolo[3',2':2,3]pyrido[4,5-d]pyrido[1,2-a]pyrimidinones [J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2808-2812.
[9]	Zhang Hao, Yu Shouyun. Visible Light-Promoted Isomerization of Alkenes [J]. Chin. J. Org. Chem., 2019, 39(1): 95-108.
[10]	Jia Qifang, Zhu Lijuan, Fan Minghui, Li Quanxin. Catalytic Pyrolysis of Lignin for Directional Production of p-Xylene over Metal Oxides-Modified HZSM-5 Catalysts [J]. Chin. J. Org. Chem., 2018, 38(8): 2101-2108.
[11]	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.
[12]	Ullah Aziz, Zhang Sheng, Bao Ming. Facile Synthesis of β-Methylstyrenes via Pd/TsOH-Catalyzed Isomerization of Allylbenzenes [J]. Chin. J. Org. Chem., 2017, 37(5): 1278-1283.
[13]	Zhong Yexin, Ren Kai, Xie Xiaomin, Zhang Zhaoguo. Transition Metal Catalyzed Isomerization Reaction of Allylic Alcohols [J]. Chin. J. Org. Chem., 2016, 36(2): 258-273.
[14]	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.
[15]	Yang Zonglian, Liao Peiqiu, Li Xingqi, Bi Xihe. Pentynenones Formation through Copper Catalyzed Coupling- Isomerization Reaction between Alkynyl Bromides and Propargylic Alcohols [J]. Chin. J. Org. Chem., 2015, 35(3): 610-617.