Chlorination of α-Cyanoketones and 1, 3-Dicarbonyl Compounds by Using Trichloroisocyanuric Acid as Chlorine Source

doi:10.6023/cjoc201712042

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (6): 1454-1461.DOI: 10.6023/cjoc201712042 Previous Articles Next Articles

Articles

三氯异氰尿酸作为氯源实现α-氰基酮和1,3-二羰基类化合物的氯化

苏瀛鹏, 石娅, 常兵兵, 吴丽丽, 种思颖, 张为钢, 黄丹凤, 王克虎, 胡雨来

西北师范大学化学化工学院兰州 730070

收稿日期:2017-12-28 修回日期:2017-12-28 发布日期:2018-02-28
通讯作者: 苏瀛鹏,E-mail:suyp51@nwnu.edu.cn E-mail:suyp51@nwnu.edu.cn
基金资助:
国家自然科学基金（Nos.21362033，21502154）和甘肃省科技计划（No.17JR5RA073）资助项目.

Chlorination of α-Cyanoketones and 1, 3-Dicarbonyl Compounds by Using Trichloroisocyanuric Acid as Chlorine Source

Su Yingpeng, Shi Ya, Chang Bingbing, Wu Lili, Chong Siying, Zhang Weigang, Huang Danfeng, Wang Kehu, Hu Yulai

College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Received:2017-12-28 Revised:2017-12-28 Published:2018-02-28
Contact: 10.6023/cjoc201712042 E-mail:suyp51@nwnu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21362033, 21502154) and the Gansu Provincial Science and Technology Program (No. 17JR5RA073).

1. Chlorination of α-Cyanoketones and 1, 3-Dicarbonyl Compounds by Using Trichloroisocyanuric Acid as Chlorine Source.PDF(8349KB)

Abstract

Cite this article

Su Yingpeng, Shi Ya, Chang Bingbing, Wu Lili, Chong Siying, Zhang Weigang, Huang Danfeng, Wang Kehu, Hu Yulai. Chlorination of α-Cyanoketones and 1, 3-Dicarbonyl Compounds by Using Trichloroisocyanuric Acid as Chlorine Source[J]. Chin. J. Org. Chem., 2018, 38(6): 1454-1461.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Roman, B. I.; Kimpe, N. D.; Stevens, C. V. Chem. Rev. 2010, 110, 5914.
[2] Dickenson, E. V.; Summers, R. S.; Croue, J.-P.; Gallard, H. Environ.Sci.Technol. 2008, 42, 3226.
[3] (a) Yang, D.; Yan, Y-L.; Liu, B. J.Org. Chem. 2002, 67, 7429.
(b) Liu, Z.; Rong, G. Chin.J.Org.Chem. 1986, 6, 363(in Chinese). (刘铸晋, 荣国斌, 有机化学, 1986, 6, 363.)
[4] Gloria, P. M. C.; Prabhakar, S.; Lobo, A. M. Tetrahedron Lett. 2008, 49, 7355.
[5] Surmont, R.; Verniest, G.; Kimpe, N. D. Org. Lett. 2010, 12, 4648.
[6] Shi, M.; Zhan, G.; Zhou, S.; Du, W.; Chen, Y. Org. Lett. 2016, 18, 6480.
[7] Tang, L.; Negrerie, D. Z.; Du, Y.; Zhao, K. Synthesis 2014, 46, 1621.
[8] Umland, K-D.; Mayer, C.; Kirsch, S. F. Synlett 2014, 25, 813.
[9] Tilstam, U.; Weinmann, H. Org.Process Res.Dev. 2002, 6, 384.
[10] Luca, L. D.; Giacomelli, G.; Porcheddu, A. Org.Lett. 2001, 3, 3041.
[11] Ashtekar, K. D.; Marzijarani, N. S.; Jaganathan, A.; Holmes, D.; Jackson, J. E.; Borhan, B. J.Am.Chem.Soc. 2014, 136, 13355.
[12] Zhang, W.; Su, Y.; Wang, K.-H.; Wu, L.; Chang, B.; Shi, Y.; Huang, D; Hu, Y. Org.Lett. 2017, 19, 376.
[13] Luca, L. D.; Giacomelli, G. Synlett 2004, 2180.
[14] Luca, L. D.; Giacomelli, G.; Nieddu, G. Synlett 2005, 223.
[15] Vo, T. T.; Zhang, J.; Parrish, D. A.; Twamley, B.; Shreeve, J. M. J. Am.Chem.Soc. 2013, 135, 11787.
[16] (a) Acharya, J.; Gupta, A. K.; Shakya, P. D.; Kaushik, M. P. Tetrahedron Lett. 2005, 46, 5293.
(b)Varaprath, S.; Stutts, D. H. J.Organomet.Chem. 2007, 692, 1892.
[17] (a) Oyley, J. M. D.; Aliev, A. E.; Sheppard, T. D. Angew.Chem., Int.Ed. 2014, 53, 10747.
(b) Mishra, A. K.; Nagarajaiah, H.; Moorthy, J. N. Eur.J.Org. Chem. 2015, 2733.
(c) Lied, F.; Lerchen, A.; Knecht, T.; Mu?ck-Lichtenfeld, C.; Glorius, F. ACS Catal. 2016, 6, 7839.
[18] Combe, S. H.; Hosseini, A.; Parra, A.; Schreiner, P. R. J.Org. Chem. 2017, 82, 2407.
[19] Mendonca, G. F.; Sindra, H. C.; Almeida, L. S.; Esteves, P. M.; Mattos, M. C. S. Tetrahedron Lett. 2009, 50, 473.
[20] Chong, S.; Su, Y.; Wu, L.; Zhang, W.; Ma, J.; Chen, X.; Huang, D.; Wang, K.-H.; Hu, Y. Synthesis 2016, 1359.
[21] Yu, W.; Du, Y.; Zhao, K. Org. Lett. 2009, 11, 2956.
[22] Smallridge, A. J.; Ten, A.; Trewhella, M. A. Tetrahedron Lett. 1998, 39, 5121.
[23] (a) Grill, J. M.; Ogle, J. W.; Miller, S. A. J.Org.Chem. 2006, 71, 9291.
(b) Kim, S. H.; Kim, K. H.; Hong, S. H. Angew.Chem., Int. Ed. 2014, 53, 771.

三氯异氰尿酸作为氯源实现α-氰基酮和1,3-二羰基类化合物的氯化

Chlorination of α-Cyanoketones and 1, 3-Dicarbonyl Compounds by Using Trichloroisocyanuric Acid as Chlorine Source

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 5

Recommended Articles

Metrics

Comments

[1]	Zong Wuzhong, Hu Yulai, Wang Xiaoping, Liu Jiaxin, Huang Danfeng, Wang Kehu. Study on the Chlorination Reaction of Hydrazones by Using of Trichloroisocyanuric Acid as Chloride Source [J]. Chin. J. Org. Chem., 2019, 39(5): 1396-1403.
[2]	GUO Qiao-Xia,SHEN Bao-Jian*. Organic Reaction Mediated by Highly Valent Groups 5 and 6 Metal Chlorides [J]. Chin. J. Org. Chem., 2005, 25(9): 1147-1155.
[3]	WANG Yong-Can,YE Jin-Xing,LIANG Xin-Miao*. Synthesis of α,β-Epoxy Ketones in a Water Suspension Medium [J]. Chin. J. Org. Chem., 2005, 25(08): 969-971.
[4]	Qian Dingquan;Cao Ruzhen;Liu Lunzu. Application of vilsmeier reagents in organic synthesis in recent years [J]. Chin. J. Org. Chem., 2000, 20(1): 30-43.
[5]	WANG ZHIQIN;ZHOU WENJUAN. Electrochlorination of diphenylsulfide and diphenyloxide with methylene chloride [J]. Chin. J. Org. Chem., 1988, 8(5): 462-465.