两种环氧化合物光化学反应的分析-analysis of photochemical reactions of two epoxy compounds.docxVIP

AbstractPhotochemical reactions have plaied an important role in organic synthesis. There are three main advantages of photochemical reactions when comparing with traditional organic synthesis. First, using light to initiate chemical reactions is less expensive and environmentalfriendly. Second, photochemical substrates can activate at mild condition without additional reagents, which can diminish the formation of byproducts. Moreover, complex, polycyclic, or highly functionalized structures can be obtained from simple substrates. Last but not the least, using photochemical steps can significantly improve the value of ee in the asymmetric synthesis.Firstly, we focus our attention on the photochemical reactions of ethyl 3-(2-(oxiran-2-yl)phenyl)acrylate and derivatives. Using 2-bromobenzaldehyde as substrate, through five steps of chemical reactions, the photochemical substrates were synthesized. To our delight, irradiation of ethyl 3-(2-(oxiran-2-yl) phenyl) acrylate-derivatives with 500 W UV light in benzene solution and 10 mol% La(OTf)3 as catalyst afforded seven-member lactone as the main product.Secondly, photochemical reactions of (2-methoxyphenyl) (3-phenyloxiran-2-yl)methanone and derivatives were studied. Irradiation of the photochemical substrates, which were synthesized through 3 steps of reactions, under 500 W UV light in benzenesolutionafforded1-(2-(benzyloxy)phenyl)-3-phenylpropane-1,3-dione- derivatives.Apartfromthat,wefoundthat(2-(benzyloxy)phenyl) (3-(4-methoxyphenyl)oxiran-2-yl) methanone undergoes chemical reaction upon visible light irradiation using 5 mol% Ru(bipy)3Cl2 with 2eq CBr4 as additives inacetonitrile solution ，which afforded 1-(2-(benzyloxy) phenyl)-3-bromo-3-(4-methoxyphenyl) propane -1,2-dione in good yield.Keywords: Photochemical reaction, Epoxy, Seven-member lactone，Photochemical rearrangement, Visible light目录摘要 ..............................................................................................................