Chapter 21: Rearrangement Reactions and Ring Reactions
Recommended Article : 【Organic Chemistry】 Organic Chemistry Table of Contents
1. Rearrangement Reactions
Figure 1. 1,2-hydride shift
Figure 2. 1,2-methyl shift
⑵ Pinacol Rearrangement: Intramolecular SN2 reaction leads to the inversion of configuration.
Figure 3. Pinacol rearrangement reaction mechanism
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
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
Figure 14. Curtius rearrangement mechanism
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
Figure 23. An example of Baeyer-Villiger oxidation leading to ring expansion
Figure 24. An example where the Beckmann rearrangement reaction mechanism leads to a ring expansion reaction
3. Ring Contraction Reactions
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
Figure 28. 2+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
Figure 32. Pomeranz-Fritsch 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