AlCl3-mediated aromatic phenylthiation with N-phenylthiophthalimide

N-Phenylthiophthalimide reacts with AlCl3 or TiCl4 in arenes to give phenyl thiated arenes alone via a phenylsulfenium ion intermediate, modified negle ct of diatomic overlap (MNDO) molecular orbital calculations of which revea led that the positive charge preferentially populates the sulfur atom rathe r than the phenyl group in the phenylsulfenium ion.