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溶剂N,N-二甲基甲酰胺参与的Michael加成-消除反应及其反应机理
引用本文:宋秀美,汪朝阳,傅建花,李建晓.溶剂N,N-二甲基甲酰胺参与的Michael加成-消除反应及其反应机理[J].华南师范大学学报(自然科学版),2009,1(4):75-80.
作者姓名:宋秀美  汪朝阳  傅建花  李建晓
作者单位:1.华南师范大学化学与环境学院化学系
基金项目:国家自然科学基金资助项目 
摘    要:研究5-烷氧基-3,4-二卤-2(5H)-呋喃酮与2-苯并咪唑的Michael加成-消除反应过程中,发现发生的溶剂N,N-二甲基甲酰胺(DMF)在催化剂无水乙醇钠的作用下参与的串联反应.探讨了反应时间、催化剂用量、反应温度对反应的影响,合成了四个化合物(4a-4d).通过UV、IR、 1H NMR、13C NMR、MS、元素分析对4a-4d进行结构表征,提出并通过GC-MS验证了可能的反应机理.

关 键 词:2(5H)-呋喃酮    N    N-二甲基甲酰胺    Michael加成反应    串联反应    反应机理
收稿时间:2008-10-21

THE TANDEM MICHAEL ADDITION-ELIMINATION REACTION OF 5-ALKOXY-3,4-DIHALO-2(5H)-FURANONE WITH SOLVENT DMF AND ITS REACTION MECHANISM
SONG Xiumei,WANG Zhaoyang,FU Jianhua,LI Jianxiao.THE TANDEM MICHAEL ADDITION-ELIMINATION REACTION OF 5-ALKOXY-3,4-DIHALO-2(5H)-FURANONE WITH SOLVENT DMF AND ITS REACTION MECHANISM[J].Journal of South China Normal University(Natural Science Edition),2009,1(4):75-80.
Authors:SONG Xiumei  WANG Zhaoyang  FU Jianhua  LI Jianxiao
Abstract:During the research on the tandem Michael addition-elimination reaction of 5-alkoxy-3,4-dihalo-2(5H)-furanone with 2-substituted benzimidazoles, the reaction that the solvent N,N-dimethylformamide (DMF) participated in was witnessed as an unexpected result. Based on the discussions of the synthetic conditions, such as reaction time, catalyst dosage, and reaction temperature, four compounds (4a-4d), including two novel compounds, were obtained by the reaction of 5-alkoxyl-3,4-dihalo-2(5H)-furanone with DMF in the presence of the catalyst ethanol sodium. The structure of 4a-4d was characterized by UV, IR, 1H NMR, 13C NMR, MS and elemental analysis. A possible reaction mechanism was proposed and confirmed by GC-MS.
Keywords:N
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