Lead Tetraacetate Mediated Electrochemical Synthesis inUndivided Compartment

Abstract

Initial stage of oxidation of lead acetate on Pt electrode in glacial acetate acid was studied using cyclic voltammetry and chronoamperometry. Results show that the initial oxidation kinetics corresponded to a model including progressive nucleation. With addition of benzene and under certain current density and temperature, the indirect organic electrosynthesis using lead tetraacetate as media could be carried out in one compartment and no lead metal was deposited on the counter electrode. Acetoxylation of acetophenone and oxidation of styrene were performed in this system and the yields are 68% and 35.6% respectively.

Key words: indirect electrochemical organic synthesis, sty-rene, undivided compartment, acetophenone, lead tetraacetate

Cite this article

YE Xiao-He, WANG Huan, XUE Teng, ZHANG Li, LU Jia-Xing*. Lead Tetraacetate Mediated Electrochemical Synthesis inUndivided Compartment[J]. Chin. J. Org. Chem., 2007, 27(05): 643-647.

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[2]	Du Xingpeng, Zhang Xi, Hou Fei, Liu Xiaojun, Wang Xicun, Quan Zhengjun. Iodine-Mediated Synthesis of 2-Acylquinoline from Acetophenone and 2-(Arylvinyl)aniline [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1337-1344.
[3]	Bao Kun, Wei Jun, Sheng Rong. Synthesis of α,α,γ,γ-Tetrafluoro-β-hydroxy Ketones and α-Fluoroacetophenones via 1,3-Diaryl-1,3-diketones [J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 930-937.
[4]	Wu Lili, Su Yingpeng, Chong Siying, Zhang Weigang, Huang Danfeng, Wang Kehu, Hu Yulai. Chiral Thiourea Catalyzed Asymmetric Henry Reaction: Construction of Stereogenic Center Bearing a CF₃ Group from 2,2,2-Trifluoroacetophenone Substrates [J]. Chin. J. Org. Chem., 2017, 37(4): 936-942.
[5]	Chen Cui, Qiu Huihua. Study on the α-Acetoxylation of sp³-C-H Bonds Adjacent to Carbonyl of Arones [J]. Chin. J. Org. Chem., 2016, 36(4): 826-829.
[6]	Li Ming, Ning Jiabin, Yu Le, Wen Lirong. Copper-Promoted Synthesis of Thiochromones Derivatives [J]. Chin. J. Org. Chem., 2016, 36(11): 2715-2722.
[7]	Tan Liquan, Liu Weibing, Huang Min, Yu Mei. α-Acetoxylation of Aromatic Ketones Mediated by Iodobenzene Diacetate [J]. Chin. J. Org. Chem., 2014, 34(4): 817-820.
[8]	Liu Bing, Zhou Hongyong, Li Yunqing, Wang Jiaxi. Asymmetric Transfer Hydrogenation of Acetophenone Promoted by Chitosan Ester Ruthenium Complex [J]. Chin. J. Org. Chem., 2014, 34(12): 2554-2558.
[9]	Nie Hongfen, Zhou Hongyong, Li Xiaona, Li Yunqing, Wang Jiaxi. Reductive Amination Reaction of Acetophenone Catalyzed by Ruthenium Complex [J]. Chin. J. Org. Chem., 2013, 33(11): 2412-2416.
[10]	Ren Zhenghong, Li Sheng, Zhang Xinghua, Fan Li, Zhou Guangming, Yang Dacheng. One-Pot Synthesis of N-[3-(4-Methylphenyl)-3-oxo-1-arylpropyl]ace-tamides Employing Trifluoroacetic Acid as an Efficient Catalyst [J]. Chin. J. Org. Chem., 2013, 33(05): 1047-1056.
[11]	Zhu Wei, Li Zhongzhou, Yao Lulu, Zheng Zubiao, Zou Xinzhuo. One-Pot α-Nucleophilic Fluorination of Acetophenones by DBDMH and Et₃N·3HF [J]. Chin. J. Org. Chem., 2012, 32(06): 1146-1149.
[12]	LI De-Fu, LIU Hui-Min, LIU Wei-Hua, YUAN Ming-Yue, ZHANG Dong-Nuan, ZHANG Ying-Qun. Synthesis of α-Bromoarylketones Catalyzed by Ionic Liquid under Microwave Irradiation [J]. Chin. J. Org. Chem., 2011, 31(03): 397-400.
[13]	LIN, Mei-Yu; WANG, Huan; ZHANG, Ai-Jian ; ZHANG, Gui-Rong ; LU, Jia-Xing*. Electrocarboxylation of Benzalacetophenone: Synthesis of 2,4-Diphenyl-4-oxobutanoic acid [J]. Chin. J. Org. Chem., 2008, 28(9): 1572-1577.
[14]	NI, Yan; XU, Yi; YANG, Wei ; PAN, Jiang ; XU, Jian-He*. Promoting Effect of Resin Adsorption on Asymmetric Reduction of Acetophenone Catalyzed by Rhodotorula sp. Cells [J]. Chin. J. Org. Chem., 2008, 28(12): 2137-2141.
[15]	TAO Fei-Yan,b,LI Bo-Gang^a,LIU Yan^a,LUO Ying-Gang*^,a. Facile Synthesis of 4-Acetyl-2-nitrobenzaldehyde [J]. Chin. J. Org. Chem., 2007, 27(11): 1441-1443.

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