4.1 Principles

The methods for the formation of bonds between nitrogen and aliphatic carbon can be broadly divided into two categories: (i) reaction of nucleophilic nitrogen with electrophilic carbon, and (ii) reaction of electrophilic nitrogen with nucleophilic carbon. In this section, we will try to cover some of the important reactions.

4.2 Substitution of Nitrogen Nucleophiles at Saturated Carbon

4.2.1 Ritter Reaction

Treatment of a tertiary alcohol or the corresponding alkene with concentrated sulphuric acid and a nitrile affords an amide that in acidic conditions undergoes hydrolysis to give amine. First, a

 

Mechanism

Scheme 1

tertiary carbocation is formed which is attacked by the nitrile to give a quaternary ion. The latter is decomposed by water to provide an amide which, in acidic conditions, is hydrolyzed to give an amine (Scheme 1).

Examples: