8.3.3 Schmidt Rearrangement
Carboxylic acid reacts with hydrazoic acid in the presence of conc. H2SO4 to give acid azide which is present in the form of conjugate acid eliminates nitrogen to afford isocyanate that could be converted into amine as reported Hofmann rearrangement.
The reaction is also effective with aldehydes, ketones, tertiary alcohols and substituted alkenes.
Mechanism
Examples:
