LONG-RANGE PROTON SPIN-SPIN COUPLING IN DIMETHYL SULFONE,

A wide variety of chemical and spectral data suggest that a sulfone group is capable of interaction with an adjacent unsaturated center however, it seems possible that the mode of this interaction may be significantly different from that of conjugation between first-row elements. To provide evidence pertinent to the problem of conjugation in sulfones, the ability of several oxygen-and sulfur-containing groups to transmit proton spin-spin couplings were compared. Similarity of the C-H coupling constants for dimethyl sulfide and dimethyl sulfone provides evidence that the sulfone is best represented by a structure with predominantly covalent sulfur-oxygen bonds. Author