Macrocyclic aromatic thioether sulfones

Abstract

Reaction of 4,4′-sulfonylbis(thiophenol) with 4,4′-dichlorodiphenyl sulfone under pseudo-high-dilution conditions leads to a novel family of all- para macrocyclic thioether sulfones [-SphiSO ₂phi-] _n (phi = 1,4-phenylene); these include a highly strained [1 + 1] cyclodimer ( n = 2), a cyclotrimer resulting from thioether exchange reactions, and a [2 + 2] cyclotetramer which can adopt two distinctly different conformations, one having molecular D _{2 d} (‘tennis-ball-seam’) symmetry, in the crystalline state.