有机化学及实验教学课件全套重排反应

1、Rearrange reactions,Chemistry Department 01 包江胤 郑睿,1.Abstract,The history is as long as organic compounds Definition: a reaction that results in a product with a different carbon skeleton from the reactant,Classification,Nucleophilic rearrangments Free radical rearrangments Electrophilic rearrangmen

2、ts Pericyclic reaction,Nucleophilic rearrangements,Eletrons on the molecular orbitals of the transition state & reactive intermidiate,2.Nucleophilic rearrangements,General rule 1)Process 2)Condition 3)Migrating group 4)Stereochemistry 5)Memory effect,1)Process,Classification 1)Carbonium ion 2)Carbon

3、yl 3)Carbene 4)Electron-defect nitrogen 5)Electron-defect oxygen 6)Aromatic series,1)Carbonium ion,(1)Rearrangements in the composition of aldehydes and ketones (2)Rearrangements of pinacols (3)Wagner-Meerweins rearrangements (4)Demyanovs rearrangements (5)Tiffeneau-Demyanovs circles expanding (6)Re

4、arrangements from dienones to phenols (7)Rearrangements with allyl groups,Rearrangements in the composition of aldehydes and ketones,33-36% O.S.，225,Rearrangements of pinacols,2)Carbonyl,Benzil-benzilic acid rearrangements (2)Rearrangements of aldehydes or ketones when catalysised by acid,Benzil-Ben

5、zilic acid arrangement,3)Carbene,Arndt-fistert synthesis and Wolff rearrangement (2)Other carbeness rearrangement reaction,4)Electron-defect nitrogen,(1)Beckmanns rearrangement (2)Hofmanns rearrangement (3)Curtiuss rearrangement (4)Schmidts rearrangement (5)Nebers rearrangement (6)Lossens rearrangem

6、ent,Beckmanns rearrangement,Hofmanns rearrangement,Curtiuss rearrangement,Schmidts rearrangement,Nebers rearrangement,5)Electron-defect oxygen,(1)Hydroperoxide rearrangement (2)Baeyer-Villiger rearrangement,6)Aromatic series (1)Bamberger rearrangement (2)Scommelet-hauser rearrangement (3)Simles rear

7、rangement,3.Free radical rearrangements,1,2 shift Others,(1)Barton rearrangement (2)Hofmann-Loffler-Freytag rearrangement,Bartons rearrangement,4.Electrophilic rearrangements,1) Aliphatic rearrangements (1)Farorskii rearrangements (2)Grovenatein-Zimmerman rearrangements (3)Stevens rearrangements (4)

8、Wittig rearrangements,2)Aromatic series,(1)Fries rearrangement (2)Aromatic ether rearrangement (3)Orton rearrangement (4)N-nitro aromatic amine rearrangement (5)Fischer-Hepp rearrangement (6)Hofmann-Martius rearrangement (7)Diazonamino compounds rearrangement,Favorskiis rearrangements,Fries rearrangements,5. Pericyclic reaction,(1)Electrocyclic reaction (2)-bonds shift (3)Cope rearrangements (4)Claisen rearrangements (5)Fischer indole synthesis (6)Benzdine rearrangements,Electrocyclic reaction,References,杜汝励，分子重排反应，人民教育出版社，1981年 王其华，有机反应机制导论