有机合成讲义PERICYCLIC REACTION1.pptVIP

Pericyclic Reaction I. Concepts and principles Pericyclic reaction: formation of a cyclic compound and its reverse process in a concerted manner. No intermediate (ion or radical) exists in the process. 1. Cycloadditions 2. Electrocyclic reactions 3. Cheletropic reactions 4. Sigmatropic rearrangements 5. The ene-reaction Related theories of pericyclic reaction 1. Frontier orbital -----Fukui 2. Conservation of orbital symmetry ----Woodward and Hoffmann Frontier orbitals: HOMO: the highest occupied molecular orbital LUMO: the lowest unoccupied molecular orbital p-bonding HOMO: LUMO: Fron