Co-host: The Chemical Society of Japan, The Society of Synthetic Organic Chemistry, Japan (Cooperation)
Photosolvolysis of 2-chloro-3-phenylpropiophenone(1) was investigated in 2,2,2-trifluoroethanol. 2,3-Diphenylpropionic acid trifluoroethylester(2), 3-phenyl-2-trifluoroethoxypropiophenone(3),2-phenyl-3-trifluoroethoxypropiophenone(4) were identified by the aid of 1H-NMR spectrum and HPLC. The substituents on 3-phenyl group greatly affected the photosolvolysis products. Photo-Favorskii rearrangement was facilitated by the electron-withdrowing substituent, while the rearrangement was completely surpressed by the electron-donating substituent. These results suggest that phenacyl cation is formed by the electron transfer from 3-phenyl ring and Photo-Favorskii rearrangement undergose through the phenacyl radical.
