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Conversion of nitriles to 1° amines using LiAlH4

[ "article:topic", "Author tag:Farmer", "showtoc:no" ]
  • Page ID
    5366
  • Nitriles can be converted to 1° amines by reaction with LiAlH4. During this reaction the hydride nucleophile attacks the electrophilic carbon in the nitrile to form an imine anion. Once stabilized by a Lewis acid-base complexation the imine salt can accept a second hydride to form a dianion. The dianion can then be converted to an amine by addition of water.

    General Reaction

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    Going from reactants to products simplified

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    Example

     

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    Mechanism

    1) Nucleophilic Attack by the Hydride

     

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    2) Second nucleophilic attack by the hydride.

     

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    3) Protonation by addition of water to give an amine

     

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    Contributors

    Prof. Steven Farmer (Sonoma State University)