The Chemistry of Sultones. I. Friedel-Crafts Reactions of Sultones^1a

Abstract

4-Hydroxy-1-butanesulfonic acid sultone has been synthesized by dehydration of the corresponding hydroxysulfonic acid. Dehydration of 5-hydroxy-1-pentanesulfonic acid, however, gave 4-hydroxy-I-pentanesulfonic acid sultone. These sultones reacted readily with benzene, p-xylene, and p-dichlorobenzene in the presence of aluminum chloride to give good yields of 4-aryl-1-alkanesulfonates without any rearrangement of the entering side chain. With chlorobenzene, toluene and anisole, mixtures of substitution isomers were formed. 2-o-Hydroxyphenylethanesulfonic acid sultone was synthesized and found to be inert in the Friedel-Crafts reaction.

Sultones and Sultams

“…19 R These reactions of the sultones parallel the nucleophilic displacement reactions of alkyl sulfonate esters, and can surely be greatly extended.…”