The chemistry of the interaction of brucine with chlorine water
Department of Organic Chemistry, Faculty of Chemistry, National Autonomous University of Mexico, Mexico City (CDMX), Mexico.
Research Article
World Journal of Chemical and Pharmaceutical Sciences, 2025, 06(02), 001-004.
Article DOI: 10.53346/wjcps.2025.6.2.0023
Publication history:
Received on 22 June 2025; revised on 28 July 2025; accepted on 31 July 2025
Abstract:
In this communication the reaction route of the interaction of brucine with chlorine water is provided along with the reaction mechanism. The reaction is initiated by chlorination of the alkaloid by means of activated hypochlorous acid. The reaction occurs at the double bond followed by internal neutralization. The enamine formed eliminates a chloride ion, giving an iminium ion conjugated with an endocyclic double bond. Reaction with water originates an hemiaminal which is oxidised to lactam. Next step is 1-4 addition of hypochlorous acid; returning of electrons form an epoxide with simultaneous separation of chloride. Acid ring-opening of the oxirane and reaction with hypochlorous acid gives an alcohol and a hypochlorite. A push-pull mechanism affords a ketone, breaking of the seven-member ring, and aldehyde formation by elimination of chloride. Finally, the aldehyde is oxidised to carboxylic acid.
Keywords:
Enamine; Hypochlorous acid; Iminium ion; Oxirane; Push-pull mechanism; Ring breaking
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Copyright © 2025 Author(s) retain the copyright of this article. This article is published under the terms of the Creative Commons Attribution Liscense 4.0