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Environmentally Benign Lewis Acid Promoted [2+3] Dipolar Cycloaddition Reactions of Nitrile Imines with Alkenes in Water
Author(s) -
Dadiboyena Sureshbabu,
Hamme Ashton T.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300840
Subject(s) - cycloaddition , chemistry , lewis acids and bases , nitrile , 1,3 dipolar cycloaddition , organic chemistry , photochemistry , catalysis
Abstract Mild and environmentally benign Lewis acid promoted 1,3‐dipolar cycloaddition reactions of α‐hydrazonyl chlorides with alkenes in water are reported. In the presence of Lewis acids, these α‐hydrazonyl chlorides generate nitrile imines in situ, which then undergo reaction with a dipolarophile to furnish the corresponding cycloaddition product. 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 comparisons between the reaction times and cycloadduct yields for the aforementioned 1,3‐dipolar reactions in aqueous and organic media and the proposed role of the Lewis acid in the 1,3‐dipolar cycloaddition reaction are described.