环境友好型路易斯酸促进腈亚胺与烯烃在水中的[2+3]偶极环加成反应
Environmentally Benign Lewis Acid Promoted [2+3]-Dipolar Cycloaddition Reactions of Nitrile Imines with Alkenes in Water.
作者信息
Dadiboyena Sureshbabu, Hamme Ashton T
机构信息
Department of Chemistry and Biochemistry, College of Science, Engineering and Technology, 1400 J. R. Lynch Street, Jackson State University, Jackson MS 39217 USA, Prof. A. T. Hamme II) Homepage: http://www.jsums.edu/chemistry/ashton-t-hamme-ii/
出版信息
European J Org Chem. 2013 Nov;2013(33):7567-7574. doi: 10.1002/ejoc.201300840.
Mild and environmentally benign Lewis acid promoted 1,3-dipolar cycloaddition reactions of α-hydrazonyl chlorides with alkenes in water are reported. These α-hydrazonyl chlorides, in the presence of Lewis acids, generate nitrile imines which react with dipolarophiles to furnish the corresponding cycloaddition products. In many cases, the required times for the completion of the Lewis acid promoted 1,3-dipolar cycloaddition reactions in water were comparable to the equivalent reactions performed in an organic solvent. Analogous tetrahexylammonium chloride promoted 1,3-dipolar cycloaddition reactions were also performed. The comparison of reaction times and cycloadduct yields for the aforementioned 1,3-dipolar reactions in aqueous and organic media as well as the proposed role of the Lewis acid in the 1,3-dipolar cycloaddition reaction are described.
报道了温和且环境友好的路易斯酸促进α-酰肼基氯与烯烃在水中的1,3-偶极环加成反应。这些α-酰肼基氯在路易斯酸存在下生成腈亚胺，腈亚胺与亲偶极体反应生成相应的环加成产物。在许多情况下，路易斯酸促进的1,3-偶极环加成反应在水中完成所需的时间与在有机溶剂中进行的等效反应相当。还进行了类似的四己基氯化铵促进的1,3-偶极环加成反应。描述了上述1,3-偶极反应在水性和有机介质中的反应时间和环加成产物产率的比较以及路易斯酸在1,3-偶极环加成反应中提出的作用。
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