A Catalytic Effect of Amines on the Reaction of Arenesulfinic Acids with N,N'-Thiodiphthalimide

Article abstract of DOI:10.1246/bcsj.53.3678

In the presence of catalytic amounts of several amines, N,N'-thiodiphthalimide has been allowed to react with one or two equiv. of arenesulfinic acids in dichloromethane, thus giving N-(arylsulfonylthio)phthalimides or bis(arenesulfonyl) sulfides respectively in good yields.The arenesulfinate anion seems to be a better nucleophile against N,N'-thiodiphthalimide than arenesulfinic acid.The mechanism of the catalytic reaction will be discussed.