Aza-Claisen Rearrangement:

The Aza-Claisen rearrangement is a chemical reaction involving a nitrogen atom’s migration from one position to another within a molecule. It is named after the Claisen rearrangement, a well-known rearrangement reaction involving oxygen atoms.

Aza- Claisen Rearrangement
Aza- Claisen Rearrangement
Aza- Claisen Rearrangement
Aza- Claisen Rearrangement

The mechanism of the aza-Claisen rearrangement:

The mechanism of the aza-Claisen rearrangement involves three steps: 

Protonation: The reaction often starts with the protonation of a nitrogen atom within the molecule, make it more electrophilic. 

Rearrangement: The nitrogen atom undergoes migration, typically through a series of bond-breaking and bond-forming steps, to a new position within the molecule. This migration can result in the forming of a new C-N bond. 

Deprotonation: After the rearrangement, deprotonation may occur to regenerate the original nitrogen-containing functional group or to form a new functional group.

Aza- Claisen Rearrangement  Mechanism
Aza- Claisen Rearrangement Mechanism

Aza- Claisen Rearrangement Examples:

These are the best examples of Aza Claisen rearrangements.

Aza- Claisen Rearrangement Examples

Aza- Claisen Rearrangement Examples

Related Reaction :

  1. Prins-Pinacol Rearrangement
  2. Lossen Rearrangement
  3. Pummerer Rearrangement
  4. Smiles Rearrangement
  5. Sommelet-Hauser Rearrangement
  6. Favorskii Rearrangement
  7. Brook Rearrangement
  8. Beckmann Rearrangement
  9. Baeyer-Villiger Oxidation/Rearrangement
  10. Aza-Cope Rearrangement
  11. Aza-Wittig Reaction
  12. Baker-Venkataraman Rearrangement
  13. Benzilic Acid Rearrangement
  14. Aza-[2,3]-Wittig Rearrangement
  15. Johnson-Claisen Rearrangement
  16. Eschenmoser-Claisen Rearrangement
  17. Claisen-Ireland Rearrangement

References:

  1. Google Scholar
  2. Recent Advances in Charge-Accelerated Aza-Claisen Rearrangements

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