LEUCKART REACTION PDF

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History[ edit ] The Leuckart reaction is named in honor of its developer, the German chemist Rudolf Leuckart — He discovered that heating benzaldehyde with formamide does not produce benzylidenediformamide as anticipated, but benzylamine. Pollard and Young summarized various ways in which amines can be formed: using either formamide or ammonium formate, or both, or adding formic acid to formamide. Ammonium formate first dissociates into formic acid and ammonia. Ammonia then performs a nucleophilic attack on the carbonyl carbon.

The hydroxyl is protonated using hydrogen from formic acid, which allows for water molecule to leave. This forms a carbocation, which is resonance stabilized. The compound attacks hydrogen from the deprotonated formic acid from previous step, forming a carbon dioxide and an amine. Formamide as reagent: The scheme depicts the mechanism for the Leuckart reaction using formamide as the reducing agent.

Formamide first nucleophilically attacks the carbonyl carbon. Hydride shift occurs, resulting in loss of carbon dioxide. Ammonium ion is added forming an imine and releasing ammonia. The imine goes through hydrolysis to form the amine, which is depicted in the scheme below. Hydrolysis of imine Applications[ edit ] A notable example of the Leuckart reaction is its use in the synthesis of tetrahydro-1,4 benzodiazepinone, a molecule that is part of the benzodiazepine family.

Researchers performed the reaction via solid-phase synthesis and used formic acid as the reducing agent.

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