Reactions occurring on the methyl group of \b\,b-dichlorobutenone

Abstract

1,1,5-Trichloropent-1-en-3-one (I), 1,1-dichloro-5-(diethylamino)pent-1-en-3-one hydrochloride and 1,1-dichloro-1,4-hexadien-3-one were prepared resp. by means of chloromethylation, Mannich reaction and aldol condensation of 4,4-dichlorobut-3-en-2-one. The chloromethylation product I reacted with triethylamine to give 1,1-dichloro-1,4-pentadien-3-one (II) in ether and 1,1-dichloro-5-ethoxypent-1-en-3-one in alcohol II polymd. easily at room temperature Reaction of I with ammonia in EtOH gave pyridinone III.

Key words: CONDENSATION REACTION, ETHER, CHLOROHYDROCARBON, ETHANOL P, MANNICH REACTION, PENTADIENE P, PYRIDINONE P, KETENE, BUTENONE P, HEXADIENE P

CLC Number:

O621

Cite this article

HE SENGQUAN. Reactions occurring on the methyl group of \b\,b-dichlorobutenone[J]. Acta Chimica Sinica, 1987, 45(3): 295-297.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Chenyu Liao, Shanwei Guo, Meiwei Huang, Yong Guo, Qing-Yun Chen, Chao Liu, Yunwen Zhang. Synthesis and Properties of Fluoroether Phosphocholine [J]. Acta Chimica Sinica, 2024, 82(1): 46-52.
[2]	Wang Jun, Xu Xiaomei, Zhou Jiaolong, Zhao Yanan, Sun Xiuli, Tang Yong, He Sufang, Yang Hongmei. Synthesis of New Sulfur-free and Phosphorus-free Ether-ester and Study on Its Properties As Ashless Friction Modifier [J]. Acta Chimica Sinica, 2023, 81(5): 461-468.
[3]	Dongxu Li, Xiang Xu, Jiage Song, Songting Liang, Yuang Fu, Xinhui Lu, Yingping Zou. Rotaxane Structure Optimizes the Photovoltaic Performance of Polymer Solar Cells^★ [J]. Acta Chimica Sinica, 2023, 81(11): 1500-1507.
[4]	Wenjing Hu, Jiusheng Li. Synthesis of Bis/triaza Crown Ethers and Study of Their Properties as Friction Modifiers^※ [J]. Acta Chimica Sinica, 2022, 80(3): 310-316.
[5]	Yinghui Wang, Simin Wei, Jinwei Duan, Kang Wang. Mechanism of Silyl Enol Ethers Hydrogenation Catalysed by Frustrated Lewis Pairs: A Theoretical Study [J]. Acta Chimica Sinica, 2021, 79(9): 1164-1172.
[6]	Yongsheng Fang, Wenhui Li, Jianying Lin, Xing Li. Different Bonds Cleavage of Arenesulfonates: Access to Diverse Aryl Ethers [J]. Acta Chimica Sinica, 2021, 79(7): 908-913.
[7]	Guan Honghao, Chen Lei, Liu Lei. Oxidative C—H Alkynylation of Unactivated Acyclic Ethers [J]. Acta Chim. Sinica, 2018, 76(6): 440-444.
[8]	Liao Fumin, Du Yi, Zhou Feng, Zhou Jian. Au(I)/Chiral Tertiary Amine Catalyzed Tandem Olefination/Asymmetric Cyclization Reaction to Quaternary Spirocyclic Oxindoles [J]. Acta Chim. Sinica, 2018, 76(11): 862-868.
[9]	Yi Yunqiang, Wu Juan, Fang Zhanqiang. Identification Influence Mechanism of Humic Acid in the Degradation of Decabromodiphenyl Ether by the BC@Ni/Fe Nanoparticles [J]. Acta Chim. Sinica, 2017, 75(6): 629-636.
[10]	Zhu Xin, Zhu Kai, Sun Bangjin, Fan Jian, Zhou Yi, Song Bo. Comprehensive Study of the Effect of DPE Additive on Photovoltaic Performance of 5,6-Difluoro-benzo[1,2,5]thiadiazole Based Donor-acceptor Copolymers [J]. Acta Chim. Sinica, 2017, 75(5): 464-472.
[11]	Shi Minglin, Zhan Gu, Du Wei, Chen Yingchun. Direct Asymmetric Aza-Vinylogous Mannich Reaction of Nitrones from Isatins and Ketimines [J]. Acta Chim. Sinica, 2017, 75(10): 998-1002.
[12]	Tian Ye, Ju Benzhi, Zhang Shufen. Synthesis and Self-Assembly Behavior of Temperature Responsive 2-Hydroxy-3-Isopropoxypropyl Hydroxyethyl Cellulose [J]. Acta Chim. Sinica, 2016, 74(4): 369-374.
[13]	Jiang Long, Cheng Bingchuan, Li Yu. Effect Analysis of Substituent Characteristics of PBDEs on Its Ah Receptor Binding Affinities [J]. Acta Chimica Sinica, 2014, 72(6): 743-750.
[14]	Geng Haobing, Chen Shanshan, Sun Xi, Zhang Xiuli, Wang Lei. Copper-Catalyzed Tandem Etherification Reactions of 2-(2,2-Dibromovinyl)phenol Derivatives with Phenols [J]. Acta Chimica Sinica, 2014, 72(5): 595-601.
[15]	Du Le, Cao Peng, Liao Jian. Bifunctional Ligand Promoted Pd-Catalyzed Asymmetric Allylic Etherification/Amination [J]. Acta Chimica Sinica, 2013, 71(9): 1239-1242.

β,β-二氯丁烯酮甲基上的反应