Explore the Curtius rearrangement, a classic organic reaction that converts carboxylic acids to amines via acyl azide and isocyanate intermediates. This guide covers:
Mechanism: Step-by-step thermal decomposition of acyl azides to isocyanates, followed by nucleophilic addition to form amines, urethanes, and ureas.
Key Features: Mild conditions, nitrogen gas evolution, and versatility in synthesizing primary amines and α-amino acids.
Applications:
Synthesis of pure primary amines (e.g., from ethyl phenyl acetate).
Preparation of α-amino acids and aldehydes (e.g., phenylacetaldehyde).
"Stepping down" carboxylic acids to shorter-chain amines.
Comparison: Contrast with Schmidt reaction and Hofmann rearrangement.
Key Highlights:
Historical Context: Discovered by Theodor Curtius (1885).
Stereospecificity: Retention of configuration during migration.
Case Studies: Industrial-scale synthesis of urethanes and ureas.
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