Vinyl sulfones

Four neutral vinyl sulfones, two of which are paired with phosphonate groups, are described. The compounds are diisopropyl (2‐phenylethenylsulfonylmethyl)phosphonate, C₁₅H₂₃O₅PS, (I), diisopropyl {2‐(7‐methoxy‐1,3‐benzodioxol‐5‐yl)ethenylsulfonyl]methylsulfonylmethyl}phosphonate, C₁₈H₂₇O₁₀PS₂, (II), bis(trans‐2‐phenylethenyl) sulfone, C₁₆H₁₄O₂S, (III), and bis(trans‐2‐phenylethenylsulfonyl)methane, C₁₇H₁₆O₄S₂, (IV). Their structures can be considered as highly functionalized mimics of mono‐, di‐ and triphosphates. These phosphate isosteres are currently of interest as agents for enzyme inhibition in both cancer and HIV therapy. All except one of the compounds has Z′ > 1. The lone exception is (IV), a disulfone with twofold crystallographic symmetry. Geometrically, the sulfone functionality is found to be a good mimic for phosphate. The principal effect of the vinyl group is to shorten the S—C(vinyl) distance relative to the S—CH₂ distance by ca 0.05 Å. The S—C—S and S—C—P backbones resemble the P—O—P backbone but are not identical because the S—C and P—C distances are longer than the P—O distance and the S—C—S and S—C—P angles are more acute than the P—O—P angle. No prior crystal structures of comparable compounds have been published.