有机合成讲义PERICYCLIC REACTION2.pptVIP

1, 3-dipolar additions 1, 3-dipole : 4 p-electrons are distributed over 3 atoms LUMO HOMO 1,3-dipole diene The reactions of 1,3-dipoles III. Electrocyclic reaction cis trans trans cis y1 y2 y3 y4 HOMO LUMO Bonding orbitals Anti-bonding orbitals HOMO conrotatory y2 heat HOMO disrotatory y3 hn y1 y2 y3 y6 y5 y4 HOMO LUMO y3 disrotatory heat HOMO y4 HOMO conrotatory hn Number of p electron 4n 4n + 2 Heat Irradiation conrotatory conrotatory disrotatory disrotatory 4 heat conrotatory dis. dis. con. IV. Sigmatropic rearrangements ? Sigmatropic arrangement 1,5-H shift Diene p-LUMO C-H s-HOMO 1. [