title: Environmentally Benign Lewis Acid Promoted [2+3]-Dipolar Cycloaddition Reactions of Nitrile Imines with Alkenes in Water.
abstract: 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 iminesin situwhich 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.
authors.affiliation: 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/
authors.forename: Sureshbabu
authors.initials: S
authors.lastname: Dadiboyena
authors.affiliation: 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/
authors.forename: Ashton T
authors.initials: AT
authors.lastname: Hamme
keywords: 1,3-Dipolar Cycloadditions; Green Chemistry; Lewis Acids; Nitrogen heterocycles; Spiro heterocycles; Spiro-pyrazolines; Surfactants