Curtius Rearrangement

What is Curtius Rearrangement?

Curtius Rearrangement is also called Curtius degradation or Curtius reaction. Curtius rearrangement is a thermal decomposition of acyl acid to form isocyanate with a loss of nitrogen as stated by Theodor Curtius in the year 1885. It is also known as Curtius degradation or Curtius reaction. This reaction is identical to the Schmidt reaction.

Isocyanates are subjected to attack by various nucleophiles namely alcohols, water, and amines which in turn output urea derivative or carbamate and essential amines.

Curtius Rearrangement

Mechanism of Curtius Rearrangement

Acyl azide preparation

Curtius Rearrangement

Decomposition

Mechanism of Curtius Rearrangement

  • Reacts with water to form an unstable carbamic acid derivative. It further undergoes spontaneous decarboxylation.

 

Curtius Rearrangement

Tautomerization

Curtius Rearrangement

Decarboxylation

  • Isocyanates are versatile starting materials. Isocyanates play a vital role in polymerization work and in the derivatisation of biomacromolecules.

Curtius Rearrangement

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