Aromatic sulphonation. Part 61. Sulphonylation in the reaction of aromatic compounds with chlorosulphuric acid in nitromethane and in dichloromethane

Abstract

Sulphonylation in the reactions of benzene, chlorobenzene, and toluene with chlorosulphuric acid in nitromethane and in dichloromethane has been studied. From the kinetic results it was concluded that the reactive electrophile in the sulphonylation in nitromethane is ArS₂O₆H₂⁺. It is proposed that this entity also leads to secondary sulphonation. For dichloromethane as solvent the observed kinetics may be explained in terms of ArS₂O₆H,ClSO₃H as the reactive sulphonylating entity.