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Conversion of nitriles to 1° amines using LiAlH4

Introduction

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)