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Chapter 21: Rearrangement Reactions and Ring Reactions

Recommended Article : 【Organic Chemistry】 Organic Chemistry Table of Contents

1. Rearrangement Reactions

2. Ring Expansion Reactions

3. Ring Contraction Reactions

4. Ring-Forming Reactions

5. Ring Opening Reactions

1. Rearrangement Reactions

⑴ Carbocation Rearrangement

Figure 1. 1,2-hydride shift

Figure 2. 1,2-methyl shift

⑵ Pinacol Rearrangement: Intramolecular S_N2 reaction leads to the inversion of configuration.

Figure 3. Pinacol rearrangement reaction mechanism

⑶ Semi-Pinacol Rearrangement

Figure 4. semi-pinacol rearrangment

Figure 5. semi-pinacol rearrangment

Figure 6. semi-pinacol rearrangment

⑷ Claisen Rearrangement Reaction

Figure 7. Claisen rearrangement reaction with allyl phenyl ether as reactant

⑸ Fries Rearrangement Reaction

⑹ Baeyer-Villiger Oxidation

Figure 8. Baeyer-Villiger oxidation mechanism

Including the hydrogen of -OH, a 7-membered ring is formed

Figure 9. Baeyer-Villiger oxidation reaction with _m_PBCA catalyst

⑺ Tiffeneau-Demjanov Rearrangement

Figure 10. Tiffeneau-Demjanov rearrangement mechanism

⑻ Johnson-Corey-Chaykovsky Reaction

Figure 11. Johnson-Corey-Chaykovsky reaction mechanism

⑼ Benzillic Acid Rearrangement

Figure 12. Benzilic Acid Rearrangement mechanism

⑽ Favoskii Rearrangement Reaction

Figure 13. Favorskii rearrangement reaction

⑾ Curtius Rearrangement

Figure 14. Curtius rearrangement mechanism

⑿ Wolff Rearrangement

Figure 15. Wolff rearrangement mechanism

⒀ Tertiary Amine Treatment for Ketene Formation

⒁ Claisen Rearrangement Reaction of Orthoester

Figure 16. Claisen rearrangement reaction of orthoester

⒂ Hoffman Rearrangement Reaction

Figure 17. Hoffman Rearrangement Reaction

⒃ Beckmann Rearrangement Reaction

Figure 18. Beckmann Rearrangement Reaction Mechanism

⒄ Cope Rearrangement Reaction

Figure 19. Grignard Coupling + Stereoselective Cope Rearrangement + Tautomerization

⒅ Anionic oxy-Cope rearrangement

Figure 20. Anionic oxy-Cope rearrangement

Figure 21. Anionic oxy-Cope rearrangement

2. Ring Expansion Reactions

⑴ Tiffeneau-Demjanov Rearrangement

Figure 22. Tiffeneau-Demjanov rearrangement mechanism

⑵ Baeyer-Villiger Oxidation

Figure 23. An example of Baeyer-Villiger oxidation leading to ring expansion

⑶ Beckmann Rearrangement

Figure 24. An example where the Beckmann rearrangement reaction mechanism leads to a ring expansion reaction

3. Ring Contraction Reactions

⑴ Favorskii Rearrangement

Figure 25. An example where the Favorskii rearrangement reaction leads to a ring contraction reaction

4. Ring-Forming Reactions

⑴ Enyne Ring-forming Reaction

Figure 26. Enyne Ring-forming Reaction

Figure 27. Enyne Ring-forming Reaction

⑵ 2+2 Ring-Forming Reaction

Figure 28. 2+2 Ring-forming Reaction

⑶ 4+2 Ring-Forming Reaction

Figure 29. 4+2 Ring-forming Reaction

⑷ Other Conjugation Ring-Forming Reaction

Figure 30. Other Conjugation Ring-forming Reaction

Figure 31. Other Conjugation Ring-forming Reaction

⑸ Pomeranz–Fritsch Reaction

Figure 32. Pomeranz-Fritsch reaction

⑹ Pictet-Spengler Reaction

Figure 33. Pictet-Spengler reaction

⑺ Bischler-Napieralski Reaction

Figure 34. Bischler-Napieralski reaction

⑻ Robinson Annulation Reaction

Figure 35. Robinson Annulation Reaction

Figure 36. Robinson Annulation Mechanism

5. Ring Opening Reactions

⑴ Grob Fragmentation

Figure 37. Grob Fragmentation Reaction

Figure 38. Grob Fragmentation Reaction

⑵ Epoxide Ring-Opening Reaction

Figure 39. Acid-Catalyzed Epoxide Ring-Opening Reaction

Figure 40. Base-Catalyzed Epoxide Ring-Opening Reaction

⑶ Polymer Formation Reaction Using Cyclic Esters as Monomers

⑷ Polymerization Reaction via Ring-Opening of Monomeric Cyclic Amides

⑸ Polyethylene Oxide Formation Reaction

Figure 41. Polyethylene Oxide Preparation

⑹ Nylon Formation Reaction

Figure 42. Nylon 6 Preparation

Input: 2021.10.15 20:58

Modified: 2022.06.24 12:00