Transsulfonylation between Aromatic Sulfones and Arenes.

Article abstract of DOI:10.1021/jo00218a018

Transsulfonylation between various aromatic and arenes catalyzed by triflic acid at 150 deg C are described.The structural requirements for the occurence of the transsulfonylations are shown to be similar to those for the transacylations that were described earlier.However, in view of the inherent differences in the properties of aromatic ketones and sulfones with respect to conjugation of the carbonyl and sulfonyl groups with the aromatic ring, a different rationale for the transsulfonylation reactions is offered.A mechanism is suggested that rationalizes the similar structural requirements for transacylations in terms of steric relief of strain in the reactions of certain ketones and sulfones.