Analysis reveals the reaction mechanism of brucine with chlorine water, indicating the formation of key compounds and transformations during the process.
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.
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Sánchez‐Viesca et al. (2025) studied this question.
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