Synthesis of stable 2-sulfoniophenolate

A series of novel stable 2-sulfoniophenolates (5a-5e, 7a, 7b) were synthesized for the first time by the reactions of 3,7-dinitrodibenzobromolium bisulfate (3) with some sulfoxides and the reactions of 3,7-dinitrodibenzocycloiodonium salts (6a, 6b) with dimethyl sulfoxide under basic condition. Their structures were established by elemental analysis, NMR, MS, IR, etc. The role of the amine (or other basic compounds, such as NaOH, Na2CO3, etc.) in the reactions was discussed. A possible reaction mechanism was proposed, by which a dissymmetric substituted benzyne was presumed to be the reaction intermediate.