Ritter Reaction

The Ritter reaction involves the electrophilic addition of a carbenium ion or a covalent species to a nitrile, forming a nitrilium ion. This intermediate is then hydrolyzed to produce the desired amide. Various substrates, including primary, secondary, tertiary, and benzylic alcohols, as well as tert-butyl acetate, can react with nitriles in the presence of strong acids to yield amides through this reaction. The reaction accommodates a broad range of nitriles, including formonitrile (hydrogen cyanide), which can be used to synthesize formamides. These formamides serve as valuable precursors to isocyanides.

Application to Crixivan Intermediate (-)-cis-(1S,2R)-1-aminoindan-2-ol