Nucleophilic addition reaction of aromatic compounds with α-chloroglycidates in the presence of Lewis acid

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Abstract

The epoxide 1 obtained by the Darzens condensation reaction of aldehydes with methyl dichloroacetate, reacted with aromatic compounds in the presence of aluminium chloride to afford α-aryl-β-chloro-α-hydroxyalkanoate 3. The intra-molecular nucleophilic addition of epoxide 1′ gave cyclisation compound 4. The scope and limitation of these reaction were studied for various aldehydes and aromatic compounds. The reaction was also studied in the presence of aluminium chloride supported on alumina or silica gel, which is thought to be a mild Lewis acid and harmless for environment. © 2003 Elsevier Science Ltd. All rights reserved.

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Lin, J. R., Gubaidullin, A. T., Mamedov, V. A., & Tsuboi, S. (2003). Nucleophilic addition reaction of aromatic compounds with α-chloroglycidates in the presence of Lewis acid. Tetrahedron, 59(10), 1781–1790. https://doi.org/10.1016/S0040-4020(03)00117-0

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