The 9,10-dicyanoanthracene and rose bengal sensitized photooxygenation of phenyl substituted ethylenes,such as tetraphenylethylene; 1,1-diphenylethylene; trans-stilbene and a,a'-dimethylstilbene,on the surface of silica gel was investigated.Photooxygenation products were characterized using comparation with authentic samples.The product distribution of photooxygenation reaction were measured.These results indicate photooxygenation reaction in these cases proceeds via the singlet oxygen pathway.