高等有机化学之重排反应.ppt

Question 读书报告 选择一个有关亲核取代反应、消除反应、周环反应、重排反应等课题做读书报告。以PPT形式上交。 要求：题目宜小，内容要深入，参考文献齐备。 PPT的文件名统一为 姓名+内容（如张三 富勒烯） * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * Group moved as the following order: tertiary alkyl＞aryl＞H＞secondary alkyl ＞primary alkyl＞methyl The cumene hydroperoxide rearrangement is quite resemble the Baeyer-Villiger Rearrangement Hydroperoxide rearrangement Important industrial reaction for manufacturing phenol and acetone III Electrophilic Rearrangement Electrophilic rearrangement is not so common as nucleophilic rearrangement The transition state is: 1 Favorskii Rearrangement Mechanism of Favorskii Rearrangement For asymmetric cycloprapanone, the stable anion form dominantly Different α- chloroketone form same rearrangement product: Intramolecular SN2 attack(structure maintaining): 2 Stevens Rearrangement Structure maintaining The sulfonium cation does the same Sommelet Rearrangement 3 Wittig Rearrangement Fries Rearrangement IV Radical Rearrangement Usually the aryl, alkenyl and acetoxy can shift * * * * * * * Chapter 8 Molecular Rearrangements I Classification of Rearrangement Reactions II Nucleophilic Rearrangement 1 Wagner-Meerwein rearrangement 2 Pinacolic Rearrangement 3 α-ethandione Rearrangement 4 Beckmann Rearrangement 5 Baeyer-Villiger Rearrangement III Electrophilic Rearrangement 1 Favorskii Rearrangement 2 Stevens Rearrangement 3 Wittig Rearrangement 4 Fries Rearrangement IV Radical Rearrangement I Classification of Rearrangement Reactions Molecular Rearrangements:it refers those reactions in which the carbon skeleton or the position of functional group changed. Usually the rearrangement was classified by the electron property of the moving group, such as Nucleophilic rearrangement, Electrophilic rearrangement, Radical rearrangement, etc. Nucleophilic rearrangement Electrophilic rearrangement Radical rearrangement II Nucleophilic Rearrangement 1 Wagner-Meerwein rearrangeme