Citation: SHI Yun, LI Mengsheng, DAN Yanni. Peroxidation of Benzoylimidazole[J]. Chinese Journal of Applied Chemistry, ;2018, 35(5): 511-517. doi: 10.11944/j.issn.1000-0518.2018.05.170162 shu

Peroxidation of Benzoylimidazole

College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China

Corresponding author: SHI Yun, shiyun@lzu.edu.cn
Received Date: 17 May 2017
Revised Date: 8 August 2017
Accepted Date: 6 September 2017

Fund Project: the National Natural Science Foundation of China 21101663the Gansu Province Youth Science and Technology Fund Project 1107RJYA080Supported by the National Natural Science Foundation of China(No.21101663), the Gansu Province Youth Science and Technology Fund Project(No.1107RJYA080)

Figures(2)

In this paper, the experimental methods for the synthesis of t-butyl peroxide compounds were discussed, in which benzoyl imidazole and t-butyl hydroperoxide(TBHP) were used as reactants, 1, 8-diazabicycloundec-7-ene(DBU) was used as the catalyst and acetonitrile(CH₃CN) was used as the reaction solvent. The effect of catalysts and their dosage, raw material ratios, solvents and temperature on the yield were investigated. A total of 25 target products were obtained under the optimum conditions with yields of 45%~99%. The molecular structures of the products were analyzed by nuclear magnetic resonance spectroscopy(¹H NMR and ¹³C NMR) and mass spectrometry. The method has the advantage of easily available material, easy operation, mild reaction conditions and a wide range of functional group tolerance, and has provided a new idea for the synthesis of t-butyl peroxide compounds.
- benzoylimidazole,
- t-butyl hydroperoxide,
- diazabicycloundec-ene catalyst,
- t-butyl peroxide compounds
1. [1]
  Larrivée-Aboussafy C, Jones B P, Price K E. DBU Catalysis of N, N'-Carbonyldiimidazole-Mediated Amidations[J]. Org Lett, 2010,12:324-327. doi: 10.1021/ol9026599
2. [2]
  Bryan V J, Tak-Hang C. Organometallic-Type Reactions in Aqueous Media Mediated by Indium Allylation of Acyloyl-Imidazoles and Pyrazoles Regioselective Synthesis of β, γ-Unsaturated Ketones[J]. Tetrahedron Lett, 1997,38:6493-6496. doi: 10.1016/S0040-4039(97)01512-8
3. [3]
  Kaustavmoni D, Moitree L, Baruah J B. Carbon Nitrogen Bond Cleavage by Copper(Ⅱ) Complexes[J]. Polyhedron, 2006,25(13):2525-2529. doi: 10.1016/j.poly.2006.02.019
4. [4]
  Taylor J E, Jones M D, Williams J M. N-Acyl DBN Tetraphenylborate Salts as N-Acylating Agents[J]. J Org Chem, 2012,77(6):2808-18. doi: 10.1021/jo202647f
5. [5]
  Heller S T, Fu T, Sarpong R. Dual Brønsted Acid/Nucleophilic Activation of Carbonylimidazole Derivatives[J]. Org Lett, 2012,14:1970-1973. doi: 10.1021/ol300339q
6. [6]
  Aggarwal V K, Andrea M. Superior Amine Catalysts for the Baylis Hillman Reaction:The Use of DBU and Its Implications[J]. Chem Commun, 1999,0:2311-2312.
7. [7]
  Shieh W C, Lozanov M, Loo M. DABCO- and DBU-accelerated Green Chemistry for n-, o-, and s-Benzylation with Dibenzyl Carbonate[J]. Tetrahedron Lett, 2003,44(24):4563-4565. doi: 10.1016/S0040-4039(03)00992-4
8. [8]
  Carafa M, Mesto E, Quaranta E. DBU-Promoted Nucleophilic Activation of Carbonic Acid Diesters[J]. Eur J Org Chem, 2011,13(13):2458-2465.
9. [9]
  Wei W, Zhang C, Xu Y. Synthesis of tert-Butyl Peresters from Aldehydes by Bu₄NI-Catalyzed Metal-Free Oxidation and Its Combination with the Kharasch-Sosnovsky Reaction[J]. Chem Commun, 2011,47(38):10827-10829. doi: 10.1039/c1cc14602e
10. [10]
  Morri A K, Thummala Y, Doddi V R. The Dual Role of 1, 8-Diazabicyclo[5.4.0]Undec-7-Ene in the Synthesis of Terminal Aryl- and Styryl-Acetylenes via Umpolung Reactivity[J]. Org Lett, 2015,17(18):4640-4643. doi: 10.1021/acs.orglett.5b02398
1. [1]
  Jichao XU , Ming HU , Xichang CHEN , Chunhui WANG , Leichen WANG , Lingyi ZHOU , Xing HE , Xiamin CHENG , Su JING . Construction and hydrogen peroxide-activated chemodynamic activity of ferrocene?benzoselenadiazole conjugate. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1495-1504. doi: 10.11862/CJIC.20250144
2. [2]
  Liu Lin , Zemin Sun , Huatian Chen , Lian Zhao , Mingyue Sun , Yitao Yang , Zhensheng Liao , Xinyu Wu , Xinxin Li , Cheng Tang . Recent Advances in Electrocatalytic Two-Electron Water Oxidation for Green H₂O₂ Production. Acta Physico-Chimica Sinica, 2024, 40(4): 2305019-0. doi: 10.3866/PKU.WHXB202305019
3. [3]
  Zhuoya WANG , Le HE , Zhiquan LIN , Yingxi WANG , Ling LI . Multifunctional nanozyme Prussian blue modified copper peroxide: Synthesis and photothermal enhanced catalytic therapy of self-provided hydrogen peroxide. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2445-2454. doi: 10.11862/CJIC.20240194
4. [4]
  Zhaoyu Wen , Na Han , Yanguang Li . Recent Progress towards the Production of H₂O₂ by Electrochemical Two-Electron Oxygen Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(2): 2304001-0. doi: 10.3866/PKU.WHXB202304001
5. [5]
  Yu Dai , Xueting Sun , Haoyu Wu , Naizhu Li , Guoe Cheng , Xiaojin Zhang , Fan Xia . Determination of the Michaelis Constant for Gold Nanozyme-Catalyzed Decomposition of Hydrogen Peroxide. University Chemistry, 2025, 40(5): 351-356. doi: 10.12461/PKU.DXHX202407052
6. [6]
  Jingping Li , Suding Yan , Jiaxi Wu , Qiang Cheng , Kai Wang . Improving hydrogen peroxide photosynthesis over inorganic/organic S-scheme photocatalyst with LiFePO₄. Acta Physico-Chimica Sinica, 2025, 41(9): 100104-0. doi: 10.1016/j.actphy.2025.100104
7. [7]
  Kangjuan Cheng , Chunxiao Liu , Youpeng Wang , Qiu Jiang , Tingting Zheng , Xu Li , Chuan Xia . Design of noble metal catalysts and reactors for the electrosynthesis of hydrogen peroxide. Acta Physico-Chimica Sinica, 2025, 41(10): 100112-0. doi: 10.1016/j.actphy.2025.100112
8. [8]
  Ke Li , Chuang Liu , Jingping Li , Guohong Wang , Kai Wang . Architecting Inorganic/Organic S-Scheme Heterojunction of Bi₄Ti₃O₁₂ Coupling with g-C₃N₄ for Photocatalytic H₂O₂ Production from Pure Water. Acta Physico-Chimica Sinica, 2024, 40(11): 2403009-0. doi: 10.3866/PKU.WHXB202403009
9. [9]
  Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-0. doi: 10.3866/PKU.WHXB202407005
10. [10]
  Fan Fan , Hao Xiu , Yuting Wang , Yongpeng Cui , Yajun Wang . Construction of NH₂-MIL-125/Na-doped g-C₃N₄ composite S-scheme heterojunction and its performance in photocatalytic hydrogen peroxide production. Acta Physico-Chimica Sinica, 2026, 42(2): 100143-0. doi: 10.1016/j.actphy.2025.100143
11. [11]
  Jiaxi Xu , Yuan Ma . Influence of Hyperconjugation on the Stability and Stable Conformation of Ethane, Hydrazine, and Hydrogen Peroxide. University Chemistry, 2024, 39(11): 374-377. doi: 10.3866/PKU.DXHX202402049
12. [12]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
13. [13]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
14. [14]
  Yuhang Zhang , Yi Li , Yuehan Cao , Yingjie Shuai , Yu Zhou , Ying Zhou . Regulating the formation type by Ir of intermediates to suppress product overoxidation in photocatalytic methane conversion. Acta Physico-Chimica Sinica, 2026, 42(2): 100173-0. doi: 10.1016/j.actphy.2025.100173
15. [15]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
16. [16]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
17. [17]
  Yan Kong , Wei Wei , Lekai Xu , Chen Chen . Electrochemical Synthesis of Organonitrogen Compounds from N-integrated CO₂ Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2307049-0. doi: 10.3866/PKU.WHXB202307049
18. [18]
  Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-Based Photocatalysts for CO₂ Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-0. doi: 10.3866/PKU.WHXB202406029
19. [19]
  Hailang JIA , Pengcheng JI , Hongcheng LI . Preparation and performance of nickel doped ruthenium dioxide electrocatalyst for oxygen evolution. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1632-1640. doi: 10.11862/CJIC.20240398
20. [20]
  Jiayi Yang , Jianxiu Hao , Huacong Zhou , Quansheng Liu . “Gorgeous Transformation” of Carbon Dioxide into Cyclic Carbonates: Catalyst Types and Roles. University Chemistry, 2026, 41(2): 178-189. doi: 10.12461/PKU.DXHX202502105

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(769)
HTML views(121)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142