Two Cascade Processes Initiated by the Insertion of Benzyne into the Se=O Bond

Two sets of cascade processes have been realized, both of which were initiated with a benzyne insertion into the Se=O bond. The key factors to differentiate these processes are based on the structures of diaryl selenium oxides and reaction conditions. When diaryl selenium oxides containing an ortho weak Sigma- electron-withdrawing group were used, triarylselenonium salts were obtained at room temperature, while ortho-(aryloxy)phenyl phenyl selanes could be produced from diaryl selenium oxides at 100 degrees C.