The α-thiocarbocation generated from the Pummerer reaction of N-methyl-N-phenyl-2-[2- (toluene-4-sulfinyl) phenyl] acetamide undergoes Friedel-Crafts reaction at the γ-carbon with the tethered aromatic ring. Reductive removal of the phenylthio group from the resulting product using Raney nickel occurs in high yield, and the overall reaction represents a new method for the synthesis of a variety of 3-phenyl-substituted oxindoles. Treatment of the ...
