Ritter reaction

The Ritter reaction is a name reaction in organic chemistry and named after the American chemist John Joseph Ritter. It is used for synthesis of N- alkyl amides from nitriles. To substrates are needed which can form carbenium ions (such as various alkylating agents in the presence of strong mineral acids). Primary, secondary and tertiary alcohols and benzyl alcohol, and tert -butyl acetate and isobutylene react very well as an alkylating agent.

Recently, it has been possible to carry out the Ritterrekation with cycloalkanes, in the presence of a strong oxidant, a copper catalyst and of a Lewis acid with high yields of carboxylic acid amides.

Reaction mechanism

The Ritter reaction is described in this section using the example of a tertiary alcohol 1. The first reaction step is initiated by a protonation of the hydroxy group in 1, to obtain a three carbenium ion as the alkylating agent after elimination of water. This is followed by a nucleophilic attack of the nitrile. The resulting Nitrilion 4 is hydrolyzed with water. After a proton rearrangement and the subsequent loss of a proton, the desired amide 8 is obtained.