Module 4: Formation of Aliphatic Carbon-Nitrogen Bonds

Lecture 11 : Carbon-Nitrogen Bonds Formation - II

4.3.1.6 Schweizer Allyl Amine Synthesis

This reaction involves the combined use of Gabriel and Wittig chemistry for the synthesis of allyl amines from phthalimide, vinyl phosphonium salt and aldehyde in the presence of base.

Mechanism

4.3.1.7 Borche Reduction

Aldehydes and ketones react with amines to give imine that could be reduced using MCNBH3(M= Li, Na) to amines.

Mechanism

The success of this method rests on the much greater reactivity of imine salt compared to carbonyl group of aldehydes and ketone to the reducing agent.

Examples: