Waiting
Processando Login

Trial ends in Request Full Access Tell Your Colleague About Jove

19.14: Preparation of 1° Amines: Azide Synthesis

TABLE OF
CONTENTS
JoVE Core
Organic Chemistry

É necessário ter uma assinatura JoVE para assistir este Faça login ou comece sua avaliação gratuita.

Education
Preparation of 1° Amines: Azide Synthesis
 
TRANSCRIPT

19.14: Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.

Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum hydride, or by catalytic hydrogenation to primary amines. The driving force for such reactions is the elimination of nitrogen gas.

Azide synthesis also works with other electrophiles like epoxides to produce amino alcohols through stereoselective ring-opening reactions. Alkyl azides have an explosive nature and must be carefully handled.

Tags

Keywords: 1° Amine Synthesis Azide Synthesis Alkyl Halides Alkyl Azides Nucleophilic Substitution Hydride Reduction Catalytic Hydrogenation Amino Alcohols Stereoselective Ring-opening Explosive Nature

Get cutting-edge science videos from JoVE sent straight to your inbox every month.

Waiting X
Simple Hit Counter