有机合成讲义REARRANGEMENTS1.pptVIP

Molecular Rearrangements Alteration of molecular backbone I. Introduction Types of rearrangement 1. Nucleophilic rearrangement: with a pair of electrons in W 2. Electrophilic rearrangement: without electron in W 3. Free radical rearrangement: with a single electron in W II. Nucleophilic rearrangement: ----rearrangement to electron-deficient carbon Driving force: formation of more stable carbonium Driving force: formation of less strained ring Wagner-Meerwein rearrangement Generation of carbonium ion 1. From a halide, by treatment with Lewis acid, eg. Ag+ or HgCl2 2. From an alcohol, by treat