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Robinson Annulation

Definition: What is Robinson Annulation?

Robinson annulation is an organic chemical reaction used to construct a six-membered ring structure. This method uses a ketone and an α, β-unsaturated ketone to form a bicyclic system containing a substituted cyclohexenone system in a sequential combination of Michael addition and intramolecular aldol condensation. The word ‘annulation’ means ‘building a ring.’ [1-5]

Robinson Annulation

The history of this chemical reaction goes back to 1935 when British organic chemist and Nobel laureate Robert Robinson created a six-member ring by forming three new carbon-carbon bonds.

Examples of Robinson Annulation [6]

Robinson Annulation Examples

Mechanism of Robinson Annulation [6-8]

Robinson Annulation Mechanism Michael Addition

Robinson Annulation Mechanism Aldol Condensation

Applications of Robinson Annulation [4,6]

Robinson annulation is used in the synthesis of various useful products such as antibiotics and steroids. Cyclohexenone and its derivatives prepared through this method are used in various natural products.

References

  1. Definition – Chem.ucla.edu
  2. Definition – Chem.libretexts.org
  3. Definition and mechanism – Ochempal.org
  4. Definition and mechanism – Byjus.com
  5. Definition and mechanism – Chemistryscore.com
  6. Mechanism – Masterorganicchemistry.com
  7. Mechanism – Name-reaction.com
  8. Mechanism – Chem.ucalgary.ca

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